Organic electroluminescent element

ABSTRACT

An organic electroluminescence device includes an anode, a cathode and an emitting layer, in which the emitting layer includes a first compound and a second compound and each of the first compound and the second compound is a compound emitting thermally activated delayed fluorescence.

TECHNICAL FIELD

The present invention relates to an organic electroluminescence device.

BACKGROUND ART

When a voltage is applied to an organic electroluminescence device(hereinafter, occasionally referred to as an organic EL device), holesare injected from an anode into an emitting layer and electrons areinjected from a cathode into the emitting layer. The injected electronsand holes are recombined in an emitting layer to form excitons. Here,according to the electron spin statistics theory, singlet excitons andtriplet excitons are generated at a ratio of 25%:75%. In theclassification according to the emission principle, in a fluorescent ELdevice which uses emission caused by singlet excitons, the limited valueof an internal quantum efficiency of the organic EL device is believedto be 25%. On the other hand, in a phosphorescent EL device which usesemission caused by triplet excitons, it has been known that the internalquantum efficiency can be improved up to 100% when intersystem crossingefficiently occurs from the singlet excitons.

A technology for extending a lifetime of a fluorescent organic EL devicehas recently been improved and applied to a full-color display of amobile phone, TV and the like. However, an efficiency of a fluorescentEL device is required to be improved.

Based on such a background, a highly efficient fluorescent organic ELdevice using delayed fluorescence has been proposed and developed. Forinstance, an organic EL device using TTF (Triplet-Triplet Fusion)mechanism that is one of mechanisms for delayed fluorescence has beenproposed. The TTF mechanism utilizes a phenomenon in which singletexcitons are generated by collision between two triplet excitons.

By using delayed fluorescence by the TTF mechanism, it is consideredthat an internal quantum efficiency can be theoretically raised up to40% even in fluorescent emission. However, as compared withphosphorescent emission, the fluorescent emission is still problematicon improving efficiency. Accordingly, in order to enhance the internalquantum efficiency, an organic EL device using another delayedfluorescence mechanism has been studied.

For instance, TADF (Thermally Activated Delayed Fluorescence) mechanismis used. The TADF mechanism utilizes a phenomenon in which inverseintersystem crossing from triplet excitons to singlet excitons isgenerated by using a material having a small energy gap (ΔST) betweenthe singlet energy level and the triplet energy level. Thermallyactivated delayed fluorescence is described in, for instance, “DevicePhysics of Organic Semiconductor” Chihaya Adachi, pages 261-262, Mar.22, 2012, published by Kodansha Company Ltd.

An organic EL device using the TADF mechanism is disclosed in, forinstance, non-Patent Literature 1.

Non-Patent Literature 1 describes that green emission by the TADFmechanism can be efficiently obtained by using as a luminescent materiala compound (hereinafter, occasionally abbreviated as PXZ-TRZ) havingphenoxazine as an electron donating unit and2,4,6-triphenyl-1,3,5-triazine as an electron acceptor unit. Non-PatentLiterature 1 also describes that an organic EL device including anemitting layer in which PXZ-TRZ (luminescent material) is doped in CBP(4,4′-Bis(N-carbazolyl)-1,1′-biphenyl)(host material) emits light at anexternal quantum efficiency (EQE) of up to 12.5%.

CITATION LIST Non-Patent Literature

-   Non-Patent Literature 1: Chihaya Adachi et al. “Efficient green    thermally activated delayed fluorescence (TADF) from a    phenoxazine-triphenylazine (PXZ-TRZ) derivative”, Chemical    Communications, in 2012, 48, p. 11392-11394

SUMMARY OF THE INVENTION Problems to be Solved by the Invention

However, voltage reduction in driving the device and a longer lifetimeare required for practical use of the organic EL device.

An object of the invention is to provide an organic electroluminescencedevice requiring a low drive voltage and exhibiting a longer lifetime.

Means for Solving the Problems

According to an aspect of the invention, an organic electroluminescencedevice includes an anode, a cathode and an emitting layer, in which theemitting layer includes a first compound and a second compound, and eachof the first compound and the second compound is a compound emittingthermally activated delayed fluorescence (hereinafter, also referred toas a thermally activated delayed fluorescence compound).

According to the above aspect of the invention, an organicelectroluminescence device requiring a low drive voltage and exhibitinga long lifetime can be provided.

BRIEF DESCRIPTION OF DRAWING

FIG. 1 schematically shows an exemplary arrangement of an organicelectroluminescence device according to a first exemplary embodiment ofthe invention.

FIG. 2 is a schematic illustration of a measuring device of transitionalPL.

FIG. 3 shows an example of a decay curve of the transitional PL.

FIG. 4 schematically shows an exemplary arrangement of an organic ELdevice according to a modification of the invention.

DESCRIPTION OF EMBODIMENT(S)

An organic EL device according to an exemplary embodiment of theinvention will be described below.

First Exemplary Embodiment Arrangement(s) of Organic EL Device

An organic EL device according to a first exemplary embodiment of theinvention will be described below.

The organic EL device in the first exemplary embodiment includes a pairof electrodes and an organic layer between the pair of electrodes. Theorganic layer includes at least one layer formed of an organic compound.The organic layer may further include an inorganic compound.

In the organic EL device in the exemplary embodiment, at least one layerof the organic layer(s) is the emitting layer. Accordingly, the organiclayer may be provided by a single emitting layer. Alternatively, theorganic layer may be provided by layers employed in an organic EL devicesuch as a hole injecting layer, a hole transporting layer, an electroninjecting layer, an electron transporting layer, a hole blocking layer,and an electron blocking layer.

The following are representative structure examples of an organic ELdevice:

(a) anode/emitting layer/cathode;(b) anode/hole injecting⋅transporting layer/emitting layer/cathode;(c) anode/emitting layer/electron injecting⋅transporting layer/cathode;(d) anode/hole injecting⋅transporting layer/emitting layer/electroninjecting⋅transporting layer/cathode;(e) anode/hole injecting-transporting layer/first emitting layer/secondemitting layer/electron injecting⋅transporting layer/cathode; and(f) anode/hole injecting-transporting layer/emitting layer/blockinglayer/electron injecting, transporting layer/cathode.

While the arrangement (d) is preferably used among the abovearrangements, the arrangement of the invention is not limited to theabove arrangements.

The “hole injecting/transporting layer (or hole injecting-transportinglayer)” means “at least one of a hole injecting layer and a holetransporting layer” while the “electron injecting/transporting layer (orelectron injecting⋅transporting layer)” means “at least one of anelectron injecting layer and an electron transporting layer.” Herein,when the hole injecting layer and the hole transporting layer areprovided, the hole injecting layer is preferably adjacent to the anode.When the electron injecting layer and the electron transporting layerare provided, the electron injecting layer is preferably adjacent to thecathode. Moreover, each of the hole injecting layer, hole transportinglayer, electron transporting layer and electron injecting layer may beprovided by a single layer or a plurality of layers.

In the exemplary embodiment, the electron transporting layer means anorganic layer having the highest electron mobility among organiclayer(s) providing an electron transporting zone existing between theemitting layer and the cathode. When the electron transporting zone isprovided by a single layer, the single layer is the electrontransporting layer. Moreover, a blocking layer having an electronmobility that is not always high may be provided as shown in thearrangement (f) between the emitting layer and the electron transportinglayer in order to prevent diffusion of excitation energy generated inthe emitting layer. Thus, the organic layer adjacent to the emittinglayer is not always an electron transporting layer.

FIG. 1 schematically shows an arrangement of an organic EL deviceaccording to the exemplary embodiment.

An organic EL device 1 includes a light-transmissive substrate 2, ananode 3, a cathode 4 and an organic layer 10 disposed between the anode3 and the cathode 4.

The organic layer 10 includes an emitting layer 5 containing a firstcompound and a second compound. The organic layer 10 also includes ahole injecting/transporting layer 6 between the emitting layer 5 and theanode 3. The organic layer 10 further includes an electroninjecting/transporting layer 7 between the emitting layer 5 and thecathode 4.

Emitting Layer

In the organic EL device 1 in the first exemplary embodiment, the firstand second compounds used in the emitting layer 5 are compounds emittingdelayed fluorescence (hereinafter, also referred to as a “delayedfluorescence compound”). The first compound and the second compoundcontained in the emitting layer 5 have mutually different molecularstructures. The emitting layer 5 preferably has no phosphorescent metalcomplex. The organic EL device in the first exemplary embodiment emitsthermally activated delayed fluorescence. The organic EL device emittingthermally activated delayed fluorescence is advantageous that a luminousefficiency similar to a luminous efficiency of a phosphorescent organicEL device can be probably achieved without using an expensive transitionmetal complex. Accordingly, a transition metal complex observed to emitphosphorescence is preferably not used in the first exemplaryembodiment. However, use of a metal complex is not necessarilyprohibited. For instance, there has been known an inexpensive metalcomplex exhibiting thermally activated delayed fluorescence with use ofa copper complex (JP-A-2011-213643). The use of a metal complexexhibiting thermally activated delayed fluorescence is not prohibited.In other words, an organic metal complex is provided by not only aphosphorescent complex but also a metal complex exhibiting thermallyactivated delayed fluorescence. In the first exemplary embodiment, anorganic EL device with use of an organic material exhibiting thermallyactivated delayed fluorescence is provided. A material exhibitingthermally activated delayed fluorescence is exemplified by a compounddescribed in “Device Physics of Organic Semiconductor” Chihaya Adachi,pages 261-262, Mar. 22, 2012, published by Kodansha Company Ltd.

In the first exemplary embodiment, it is preferable that a differencebetween singlet energy EgS(M1) of the first compound and singlet energyEgS(M2) of the second compound is 0.3 eV or less. In other words, it ispreferable to satisfy a relationship of |EgS(M1)−EgS(M2)|≤0.3 eV. It ismore preferable to satisfy a relationship of |EgS(M1)−EgS(M2)|≤0.2 eV.

In the first exemplary embodiment, it is preferable that a differencebetween energy gap Eg_(77K)(M1) at 77K of the first compound and energygap Eg_(77K)(M2) at 77K of the second compound is 0.3 eV or less. Inother words, it is preferable to satisfy a relationship of|Eg_(77K)(M1)−Eg_(77K)(M2)|≤0.3 eV. It is more preferable to satisfy arelationship of |Eg_(77K)(M1)−Eg_(77K)(M2)|≤0.2 eV.

In the first exemplary embodiment, at least one of a plurality of thethermally activated delayed fluorescence compounds contained in theemitting layer 5 is preferably a compound in which a difference ΔSTbetween singlet energy EgS and energy gap Eg_(77K) at 77K preferablysatisfies a relationship represented by a numerical formula (1)(Numerical Formula 1) below, more preferably has ΔST of less than 0.2eV.

ΔST=EgS−Eg _(77K)≤0.3 (eV)  (Numerical Formula 1)

In the first exemplary embodiment, the first compound and the secondcompound which are thermally activated delayed fluorescence compoundsare contained in the emitting layer 5. Accordingly, the first compoundis preferably a compound in which a difference ΔST(M1) between thesinglet energy EgS(M1) and the energy gap Eg_(77K)(M1) at 77K satisfiesa relationship represented by a numerical formula (1-1) below, morepreferably a compound in which ΔST(M1) is less than 0.2 eV.

ΔST(M1)=EgS(M1)−Eg _(77K)(M1)<0.3 eV  (Numerical Formula 1-1)

The second compound is preferably a compound in which a differenceΔST(M2) between the singlet energy EgS(M2) and the energy gapEg_(77K)(M2) at 77K satisfies a relationship represented by a numericalformula (1-2) below, more preferably a compound in which ΔST(M2) is lessthan 0.2 eV.

ΔST(M2)=EgS(M2)−Eg _(77K)(M2)<0.3 eV  (Numerical Formula 1-2)

It is further preferable that the first compound satisfies therelationship of the numerical formula (1-1) and the second compoundsatisfies the relationship of the numerical formula (1-2).

From quantum chemical viewpoint, decrease in the energy difference (ΔST)between the singlet energy EgS and the triplet energy EgT can beachieved by a small exchange interaction therebetween. Physical detailsof the relationship between ΔST and the exchange interaction areexemplarily described in Reference Documents 1 and 2 below:

-   Reference Document 1: Organic EL Symposium, proceeding for the tenth    meeting edited by Chihaya Adachi et al., S2-5, p 11-12; and-   Reference Document 2: Organic Photochemical Reaction Theory edited    by Katsumi Tokumaru, Tokyo Kagaku Dojin Co., Ltd. (1973).

Such a material can be synthesized according to molecular design basedon quantum calculation. Specifically, the material is a compound inwhich a LUMO electron orbit and a HOMO electron orbit are localized toavoid overlapping.

Examples of the compound having a small ΔST are compounds in which adonor element is bonded to an acceptor element in a molecule and ΔST isin a range of 0 eV or more and less than 0.3 eV in terms ofelectrochemical stability (oxidation-reduction stability).

A more preferable compound is such a compound that dipoles formed in theexcited state of a molecule interact with each other to form anaggregate having a reduced exchange interaction energy. According toanalysis by the inventors, the dipoles are oriented substantially in thesame direction in the compound, so that ΔST can be further reduced bythe interaction of the molecules. In such a case, ΔST can be extremelysmall in a range of 0 eV to 0.2 eV.

Relationship Between EgT and Eg_(77K)

Triplet energy EgT is measured as follows. A compound (measurementtarget) was deposited on a quartz substrate to prepare a sampleencapsulated in an NMR tube. A sample was prepared under the followingconditions.

quartz substrate/TH-2: measurement target compound (100 nm of thickness,12 mass % of concentration of the measurement target compound)

A phosphorescent spectrum (ordinate axis: phosphorescent luminousintensity, abscissa axis: wavelength) of each of the samples wasmeasured at a low temperature (77K). A tangent was drawn to the rise ofthe phosphorescent spectrum on the short-wavelength side. An energyamount was calculated as the energy gap Eg_(77K) at 77K according to aconversion equation 2 below based on a wavelength value λ_(edge) (nm) atan intersection of the tangent and the abscissa axis.

Eg _(77K) (eV)=1239.85/λ_(edge)  Conversion Equation 2:

For phosphorescence measurement, a spectrophotofluorometer body F-4500(manufactured by Hitachi High-Technologies Corporation) was used.

The tangent to the rise of the phosphorescence spectrum on theshort-wavelength side is drawn as follows. While moving on a curve ofthe phosphorescence spectrum from the short-wavelength side to themaximum spectral value closest to the short-wavelength side among themaximum spectral values, a tangent is checked at each point on the curvetoward the long-wavelength of the phosphorescence spectrum. Aninclination of the tangent is increased as the curve rises (i.e., avalue of the ordinate axis is increased). A tangent drawn at a point ofthe maximum inclination (i.e., a tangent at an inflection point) isdefined as the tangent to the rise of the phosphorescence spectrum onthe short-wavelength side.

The maximum with peak intensity being 15% or less of the maximum peakintensity of the spectrum is not included in the above-mentioned maximumclosest to the short-wavelength side of the spectrum. The tangent drawnat a point of the maximum spectral value being closest to theshort-wavelength side and having the maximum inclination is defined as atangent to the rise of the phosphorescence spectrum on theshort-wavelength side.

The material used in the first exemplary embodiment is preferably acompound having a small ΔST. When ΔST is small, intersystem crossing andinverse intersystem crossing are likely to occur even at a lowtemperature (77K), so that the singlet state and the triplet statecoexist. As a result, the spectrum to be measured in the same manner asthe above includes emission from both the singlet state and the tripletstate. Although it is difficult to distinguish emission from the singletstate from emission from the triplet state, the value of the tripletenergy is basically considered dominant.

Accordingly, in the exemplary embodiment, the spectrum is measured bythe same method as that for measuring a typical triplet energy, but anenergy value of the spectrum measured in the aforementioned manner isreferred to as an energy gap Eg_(77K) in order to differentiate themeasured energy from a typical triplet energy in a strict meaning.

Singlet Energy EgS

Singlet Energy EgS was obtained by the following method.

Each of the compounds was used for forming a 100 nm thick film on aquartz substrate by vacuum deposition to prepare a sample formeasurement. Emission spectrum of each sample was measured at a roomtemperature (300K). The emission spectrum was expressed in coordinatesof which ordinate axis indicated the luminous intensity and of whichabscissa axis indicated the wavelength. A tangent was drawn to the riseof the emission spectrum on the short-wavelength side, and a wavelengthvalue λedge (nm) at an intersection of the tangent and the abscissa axiswas obtained. The wavelength value was converted to an energy value bythe following conversion equation. The energy value was defined as EgS.

EgS (eV)=1239.85/λedge  Conversion Equation:

For the emission spectrum measurement, a spectrophotofluorometer bodyF-7000 (manufactured by Hitachi High-Technologies Corporation) was used.

The tangent to the rise of the emission spectrum on the short-wavelengthside was drawn as follows. While moving on a curve of the emissionspectrum from the short-wavelength side to the maximum spectral valueclosest to the short-wavelength side among the maximum spectral values,a tangent is checked at each point on the curve toward thelong-wavelength of the phosphorescence spectrum. An inclination of thetangent is increased as the curve rises (i.e., a value of the ordinateaxis is increased). A tangent drawn at a point of the maximuminclination was defined as the tangent to the rise of thephosphorescence spectrum on the short-wavelength side.

The maximum with peak intensity being 10% or less of the maximum peakintensity of the spectrum is not included in the above-mentioned maximumclosest to the short-wavelength side of the spectrum. The tangent drawnat a point of the maximum spectral value being closest to theshort-wavelength side and having the maximum inclination is defined as atangent to the rise of the emission spectrum on the short-wavelengthside.

The calculation of the singlet energy EgS and the energy gap Eg_(77K)will be described in detail later.

TADF Mechanism

As described above, when ΔST of the organic material is small, inverseintersystem crossing from the triplet energy level of the organicmaterial to the singlet energy level thereof is easily caused by heatenergy given from the outside. An energy state conversion mechanism toperform spin exchange from the triplet state of electrically excitedexcitons within the organic EL device to the singlet state by inverseintersystem crossing is referred to as TADF Mechanism.

Each of the first and second compounds used in the first exemplaryembodiment is preferably a compound having a small ΔST. Inverseintersystem crossing from the triplet energy level of the compound tothe singlet energy level thereof is easily caused by heat energy givenfrom the outside.

Delayed Fluorescence

Thermally activated delayed fluorescence is described in “Device Physicsof Organic Semiconductor” Chihaya Adachi, pages 261 to 268, published byKodansha Company Ltd. This document describes that, when an energy gapΔE₁₃ between a singlet state and a triplet state of a fluorescentmaterial can be decreased, in spite of a typical low transitionprobability, inverse energy transfer from the triplet state to thesinglet state occurs at a high efficiency to express thermallystimulated delayed fluorescence (TADF). Further, a generating mechanismof delayed fluorescence is described in FIG. 10.38 in this document. Thecompound emitting delayed fluorescence in the first exemplary embodimentis a compound emitting thermally activated delayed fluorescence to begenerated by such a mechanism.

Delayed fluorescence can be observed by measuring transitional PL.

FIG. 2 is a schematic illustration of an exemplary device for measuringthe transitional PL.

In the first exemplary embodiment, a transitional PL measuring device100 includes: a pulse laser 101 capable of irradiating light having apredetermined wavelength; a sample chamber 102 that houses a measurementsample; a spectrometer 103 that disperses light irradiated from themeasurement sample; a streak camera 104 for forming a two-dimensionalimage; and a personal computer 105 that scans and analyzes thetwo-dimensional image. A device usable for the measurement of thetransitional PL is not limited to the device described in the firstexemplary embodiment.

The sample housed in the sample chamber 102 is obtained by forming athin film, in which a doping material is doped to a matrix material at aconcentration of 12 mass %, on the quartz substrate.

The thin film sample housed in the sample chamber 102 is irradiated withpulse laser from the pulse laser 101 to be excited. Emission isextracted at 90 degrees angle relative to the excited light. Theextracted emission is dispersed with the spectrometer 103 to form atwo-dimensional image in the streak camera 104. As a result, thetwo-dimensional image expressed in coordinates of which ordinate axisindicates time and of which abscissa axis indicates a wavelength, inwhich a luminous point indicates a luminous intensity, can be obtained.If the two-dimensional image is cut out along a predetermined time axis,emission spectrum expressed in coordinates of which ordinate axisindicates a luminous intensity and of which abscissa axis indicates thewavelength can be obtained. If the two-dimensional image is cut outalong a wavelength axis, a decay curve (transitional PL) expressed incoordinates of which ordinate axis indicates a logarithm of the luminousintensity and of which abscissa axis indicates time can be obtained.

For instance, using a reference compound H1 below as the matrix materialand a reference compound D1 as the doping material, a thin film sample Awas prepared as described above and the transitional PL was measured.

Behavior of delayed fluorescence can also be analyzed based on the decaycurve obtained by measuring the transitional PL. The transitional PLmeasurement is a method for measuring reduction behavior (transitionalproperty) of PL emission obtained after irradiating pulse laser on asample to excite the sample and stopping irradiating the pulse laser. PLemission in a TADF material is divided into a luminescence componentfrom singlet excitons to be initially generated in PL excitation and aluminescence component from singlet excitons to be generated throughtriplet excitons. Lifetime of the singlet excitons initially generatedin the PL excitation is very short at a nano-second order. Accordingly,the emission from the singlet excitons is rapidly reduced after pulselaser radiation.

On the other hand, since delayed fluorescence provides emission fromsinglet excitons generated through long-life triplet excitons, emissionis gradually reduced. Thus, there is a large difference in time betweenthe emission from the singlet excitons initially generated in the PLexcitation and the emission from the singlet excitons derived from thetriplet excitons. Accordingly, a luminous intensity derived from delayedfluorescence is obtainable.

Herein, the decay curve was analyzed using the above-described thin filmsample A and a thin film sample B. The thin film sample B was preparedas described above, using a reference compound H2 below as the matrixmaterial and the reference compound D1 as the doping material.

FIG. 3 shows a decay curve obtained from the measured transitional PL ofthe thin film sample A and the thin film sample B.

An emission decay curve expressed in coordinates of which ordinate axisindicates a luminous intensity and of which abscissa axis indicates timecan be obtained by measuring the transitional PL as described above.Based on the emission decay curve, a fluorescence intensity ratiobetween fluorescence in the single state generated by light excitationand the delayed fluorescence in the singlet state generated by theinverse energy transfer through the triplet state can be estimated. Inthe delayed fluorescence material, a ratio of the delayed fluorescenceintensity to be gradually reduced is larger to some extent than a ratioof the fluorescence intensity to be rapidly reduced.

In the first exemplary embodiment, an amount of the delayed fluorescencecan be calculated using the device of FIG. 2. In the delayedfluorescence compound after excited with pulse light (light irradiatedfrom the pulse laser) having a wavelength to be absorbed in the delayedfluorescence compound, Prompt Emission that is immediately observed inthe excited state and Delay Emission that is not observed immediatelyafter the excitation but is later observed are present. In the firstexemplary embodiment, an amount of Delay Emission is preferably 5% ormore based on an amount of Prompt Emission.

The amount of Prompt Emission and the amount of Delay Emission can beobtained according to the same method as a method described in “Nature492, 234-238, 2012.” The device used for calculating the amounts ofPrompt Emission and Delay Emission is not limited to a device describedin the above document.

A sample usable for measuring delayed fluorescence is obtained, forinstance, by co-depositing a measurement target compound and a compoundTH-2 described later on a quartz substrate so that a ratio of themeasurement target compound is 12 mass %, thereby forming a 100 nm thinfilm.

Combination of Thermally Activated Delayed Fluorescence Materials

As a typical arrangement of an organic EL device, an emitting layercontains a fluorescent material and/or a phosphorescent material (adopant material) and a compound having larger singlet energy or tripletenergy than those of the dopant material (a host material).Recombination of holes and electrons in the emitting layer are roughlyclassified into two types. A first type of recombination is conducted ona host and a second type of recombination is conducted on a dopant(guest).

For the recombination on the host, the host is required to mainlytransport carriers and generate excitons on the host. The host isfurther required to disperse the guest in the film and trap excitedenergy so as not to disperse the excited energy in adjacent layers.

On the other hand, in the recombination on the guest (dopant), the guesttransports carriers and generates excitons. In this recombination, thehost is required to mainly disperse the guest in the film of theemitting layer and trap excited energy so as not to disperse the excitedenergy in adjacent layers.

Thus, a typical host is commonly required to disperse the guest in thefilm and trap excited energy so as not to disperse the excited energy inadjacent layers.

A fluorescent material and a phosphorescent material which are typicallyused in the organic EL device cause concentration quenching whencontained at a high concentration in the emitting layer. For instance,in a typical fluorescent organic EL device, when a concentration of theguest (dopant) is 10 mass % or more, a significant decrease in theluminous efficiency is caused by a phenomenon called concentrationquenching. For this reason, it is required to disperse the guest(dopant) in the film of the emitting layer using the host as describedabove. Also in a phosphorescent organic EL device, when a concentrationof the guest (dopant) is high, a decrease in the luminous efficiency iscaused although the decrease is more gradual than in the fluorescentorganic EL device.

The inventors found that a significant decrease in the luminousefficiency is not caused even when a concentration of the thermallyactivated delayed fluorescence material is high (e.g., 50 mass % ormore) in the emitting layer. Accordingly, the inventors noted a possibleorganic EL device in which the host mainly dispersing the guest in thefilm as described in prior art is not necessarily contained in theemitting layer. Consequently, the inventors confirmed based on thefindings that a drive voltage of the organic EL device can be reducedand a emission lifetime thereof can be prolonged by including thethermally activated delayed fluorescence material as the first andsecond compounds in the emitting layer instead of the host materialhaving a large triplet energy.

In a typical organic EL device, a compound having singlet energy largerthan singlet energy of a luminescent material and a compound havingtriplet energy larger than triplet energy of the luminescent materialare contained as the host in the emitting layer. Particularly, in theemitting layer including a blue emitting material, a compound having aparticularly large singlet energy or triplet energy is used. However, insuch a typical organic EL device, injection and transportation ofcarriers into the emitting layer are blocked due to a high singletenergy or triplet energy of the host, so that the drive voltage is highand the emission lifetime is short.

In the organic EL device of the first exemplary embodiment, by includingthe first compound and the second compound (both of which are materialsemitting thermally activated delayed fluorescence) in the emittinglayer, for instance, even when excited energy is dispersed from thefirst compound, the second compound absorbs the excited energy to allowthermally activated delayed fluorescence. Moreover, in the organic ELdevice in the first exemplary embodiment, an energy gap between thefirst and second compounds is preferably small for the emitting layer toexhibit blue emission. Accordingly, it is preferable that the first andsecond compounds satisfy at least one of the above relationships of|EgS(M1)−EgS(M2)|≤0.3 eV and |Eg_(77K)(M1)−Eg_(77K)(M2)|≤0.3 eV. It ismore preferable that the first and second compounds satisfy at least oneof the above relationships of |EgS(M1)−EgS(M2)|≤0.2 eV and|Eg_(77K)(M1)−Eg_(77K)(M2)≤0.2 eV. In the first exemplary embodiment, incase of a blue-emitting organic EL device, it is further preferable thatthe first and second compounds satisfy at least one of the aboverelationships of |EgS(M1)−EgS(M2)|≤0.2 eV and|Eg_(77K)(M1)−Eg_(77K)(M2)|≤0.2 eV. In case of an organic EL deviceexhibiting emission in colors (e.g., green, yellow and red) having alonger wavelength than that of blue emission, the energy relationshipsof the first and second compounds are not limited to the above.

Note that, in the exemplary embodiment, inclusion of the above typicalhosts in the emitting layer is not prohibited. A typical host may beincluded in the emitting layer as long as the first and second compoundsaccording to the exemplary embodiment are present in the emitting layer.However, the emitting layer is preferably formed of the thermallyactivated delayed fluorescence material.

In the first exemplary embodiment, at least one of the first compoundand the second compound preferably has a main peak wavelength of 500 nmor less, more preferably 480 nm or less. The main peak wavelength meansa peak wavelength of luminescence spectrum exhibiting a maximum luminousintensity among luminous spectra measured in a toluene solution in whicha compound is dissolved at a concentration from 10⁻⁵ mol/l to 10⁻⁶mol/l.

In the first exemplary embodiment, at least one of the first compoundand the second compound preferably emits thermally activated delayedfluorescence in blue.

Content Ratio of Materials in Emitting Layer

In the first exemplary embodiment, it is preferable that a concentrationof the first compound in the emitting layer 5 is 20 mass % or more and aconcentration of the second compound in the emitting layer 5 is 20 mass% or more. It is more preferable that the concentration of the firstcompound is 30 mass % or more and the concentration of the secondcompound is 30 mass % or more. A total concentration of the firstcompound and the second compound in the emitting layer is 100 mass % orless.

In the first exemplary embodiment, at least one of a plurality of thethermally activated delayed fluorescence compounds contained in theemitting layer 5 is preferably a compound represented by a formula (1)below. For instance, both of the first compound and the second compoundmay be the compound represented by the formula (1) below. However, inthis arrangement, the first compound and the second compound havemutually different molecular structures. Alternatively, for instance,one of the first compound and the second compound may be the compoundrepresented by the formula (1) below and the other of the first compoundand the second compound may be a thermally activated delayedfluorescence compound having a different structure.

In the formula (1), Cz is a group derived from a structure representedby a formula (10) below.

In the formula (10), X₁ represents a single bond, an oxygen atom, asulfur atom, a carbonyl group, NR₁, CR₂R₃, SiR₄R₅ or GeR₆R₇. In otherwords, a cyclic structure represented by the formula (10) is selectedfrom the group consisting of cyclic structures represented by formulae(10b) to (10i).

In the formulae (10), (10b) to (10i), A and B each independentlyrepresent a substituted or unsubstituted cyclic structure. When at leastone of the cyclic structure A and the cyclic structure B has a pluralityof substituents, adjacent substituents may form a ring. The ring to beformed may be a saturated or unsaturated ring. The substituent of thecyclic structures A and B is preferably an electron donatingsubstituent. Moreover, adjacent substituents preferably further form anelectron donating ring.

In the formulae (10), (10b) to (10i), when at least one of the cyclicstructure A and the cyclic structure B has a substituted orunsubstituted heterocyclic structure, the heterocyclic structure has apartial structure represented by a formula (11) below.

The group derived from the structure represented by the formula (10) ispreferably a group represented by formula (10-1) below.

In the formula (10-1), X₁ represents the same as X₁ in the formula (10).In other words, the group represented by the formula (10-1) is selectedfrom the group consisting of groups represented by formulae (10b-1) to(10i-1) below.

In the formulae (10b-1) to (10i-1), the cyclic structure A and thecyclic structure B each independently represent the same as the cyclicstructure A and the cyclic structure B in the formulae (10) and (10b) to(10i).

In the formula (1), L₁ represents a single bond, a substituted orunsubstituted (m+1)-valent aromatic hydrocarbon group or a substitutedor unsubstituted (m+1)-valent heterocyclic group.

L₂ represents a single bond, a substituted or unsubstituted (n+p)-valentaromatic hydrocarbon group or a substituted or unsubstituted(n+p)-valent heterocyclic group.

L₃ represents a single bond, a substituted or unsubstituted (o+1)-valentaromatic hydrocarbon group or a substituted or unsubstituted(o+1)-valent heterocyclic group.

In the formula (1): m is an integer of 1 to 6; n and p are eachindependently an integer of 1 to 6; and o is an integer of 1 to 6. m, n,o and p are each independently preferably an integer of 1 to 3, morepreferably 1 or 2.

In the first exemplary embodiment, L₁ is a linking group of whichvalence is determined depending on a value of m. When m is 1, L₁ is adivalent linking group. L₂ is a linking group of which valence isdetermined depending on values of n and p. When both of n and p are 1,L₂ is a divalent linking group. The same applies to the later-describedlinking groups (e.g., L₃).

In the formula (1), Az₁ is represented by a formula (12) below.

In the formula (12), X₁₁ to X₁₅ each independently represent CR₈ or anitrogen atom, in which at least one of X₁₁ to X₁₅ is a nitrogen atom.In the formula (12), one to three of X₁₁ to X₁₅ are preferably nitrogenatoms. In the formula (12), adjacent ones of R₈ may form a ring.

When a single nitrogen atom is provided, X₁₁ or X₁₅ is preferably anitrogen atom. When two nitrogen atoms are provided, X₁₁ and X₁₅ arepreferably nitrogen atoms. When three nitrogen atoms are provided, X₁₁,X₁₃ and X₁₅ are preferably nitrogen atoms. Among the above arrangements,a triazine ring in which X₁₁, X₁₃ and X₁₅ are nitrogen atoms is morepreferable in the formula (12).

In the formulae (1), (10), (10b) to (10i) and (10b-1) to (10i-1), R₁ toR₇ each independently represent a hydrogen atom or a substituent. Thesubstituent in R₁ to R₇ is selected from the group consisting of asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, a substituted or unsubstituted heterocyclic group having 5 to 30ring atoms, a substituted or unsubstituted alkyl group having 1 to 30carbon atoms, a substituted or unsubstituted alkylsilyl group having 3to 30 carbon atoms, a substituted or unsubstituted arylsilyl grouphaving 6 to 60 ring carbon atoms, a substituted or unsubstituted alkoxygroup having 1 to 30 carbon atoms, a substituted or unsubstitutedaryloxy group having 6 to 30 ring carbon atoms, a substituted orunsubstituted alkylamino group having 2 to 30 carbon atoms, asubstituted or unsubstituted arylamino group having 6 to 60 ring carbonatoms, a substituted or unsubstituted alkylthio group having 1 to 30carbon atoms, and a substituted or unsubstituted arylthio group having 6to 30 ring carbon atoms.

In the formula (12), R₈ each independently represents a hydrogen atom ora substituent. The substituent in R₈ is selected from the groupconsisting of a substituted or unsubstituted aryl group having 6 to 30ring carbon atoms, a substituted or unsubstituted heterocyclic grouphaving 5 to 30 ring atoms, a substituted or unsubstituted alkyl grouphaving 1 to 30 carbon atoms, a substituted or unsubstituted alkylsilylgroup having 3 to 30 carbon atoms, a substituted or unsubstitutedarylsilyl group having 6 to 60 ring carbon atoms, a substituted orunsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted orunsubstituted aryloxy group having 6 to 30 ring carbon atoms, asubstituted or unsubstituted alkylamino group having 2 to 30 carbonatoms, a substituted or unsubstituted arylamino group having 6 to 60ring carbon atoms, a substituted or unsubstituted alkylthio group having6 to 30 carbon atoms, and a substituted or unsubstituted arylthio grouphaving 6 to 30 ring carbon atoms.

In the first exemplary embodiment, the compound represented by theformula (1) is preferably a compound represented by a formula (13)below.

In the formula (13), X₁, a cyclic structure A and a cyclic structure Brespectively represent the same as X₁, the cyclic structure A and thecyclic structure B in the formula (10).

In the formula (13), L₂ represents the same as L₂ of the formula (1).

In the formula (13), X₁₁ to X₁₅ each independently represent the same asX₁₁ to X₁₅ of the formula (12).

The compound represented by the formula (13) is preferably compoundsrepresented by formulae (13a) to (13c) below, among which a compoundrepresented by the formula (13c) is more preferable.

In the formulae (13a) to (13c), X₁, a cyclic structure A and a cyclicstructure B respectively represent the same as X₁, the cyclic structureA and the cyclic structure B in the formula (10).

In the formulae (13a) to (13c), L₂ represents the same as L₂ of theformula (1).

In the formula (13a), X₁₁ and X₁₃ each independently represent the sameas X₁₁ to X₁₅ of the formula (12).

In the formulae (13a) to (13c), R₂₁ and R₂₂ each independently representthe same as R₈ described above.

In the compounds represented by the formulae (1), (13) and (13a) to(13c) or the groups represented by the formulae (10) and (10b) to (10g),the cyclic structure A and the cyclic structure B are exemplified by asaturated or unsaturated five-membered ring and a saturated orunsaturated six-membered ring. Among the cyclic structures, an aromatichydrocarbon ring or a heterocyclic ring are preferable, among which abenzene ring and an azine ring are more preferable and a benzene ring isfurther preferable.

Moreover, in the first exemplary embodiment, both of the cyclicstructure A and the cyclic structure B are preferably substituted orunsubstituted benzene rings, in which at least one of the benzene ringsmore preferably has a substituent. As the substituent of the benzenering, a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms and a substituted or unsubstituted heterocyclic grouphaving 5 to 30 ring atoms are preferable. Further, at least one of thecyclic structure A and the cyclic structure B preferably has asubstituent. The substituent herein is preferably an electron donatingsubstituent.

In the first exemplary embodiment, Cz of the formula (1) is preferablyrepresented by the formula (10b) and both of the cyclic structure A andthe cyclic structure B are preferably substituted or unsubstitutedbenzene rings. The substituent of the cyclic structures A and B is thesame as described above.

In the formula (10b), when one of the cyclic structure A and the cyclicstructure B is a heterocycle, the one of the cyclic structure A and thecyclic structure B preferably has the partial structure represented bythe formula (11). It is preferable that the cyclic structure A and thecyclic structure B in the formula (10b) are each a six-memberedheterocycle having the partial structure represented by the formula(11).

In the first exemplary embodiment, the compound represented by theformula (1) is preferably a compound represented by a formula (14)below.

In the formula (14), L₁, L₂, L₃, m, n, o and p respectively representthe same as L₁, L₂, L₃, m, n, o and p of the formula (1).

In the formula (14), X₁₁ to X₁₅ each independently represent the same asX₁₁ to X₁₅ of the formula (12).

In the formula (14), R₃₁ and R₃₂ each independently represent the sameas R₈ described above. Adjacent ones of R₃₁ may form a ring. Adjacentones of R₃₂ may form a ring.

In the formula (14), q and r are 4.

In the first exemplary embodiment, the compound represented by theformula (1) is preferably a compound represented by a formula (16)below. In other words, in the compound represented by the formula (14),it is preferable that L₁ and L₃ are each a single bond and n, o and pare 1.

In the formula (16), L₂ and m respectively represent the same as L₂ andm of the formula (1).

In the formula (16), X₁₁ to X₁₅ each independently represent the same asX₁₁ to X₁₅ of the formula (12).

In the formula (16), R₃₁ and R₃₂ each independently represent the sameas R₈ described above. Adjacent ones of R₃₁ may form a ring. Adjacentones of R₃₂ may form a ring.

In the formula (16), q and r are 4.

In the first exemplary embodiment, the compound represented by theformula (16) is preferably a compound represented by a formula (17)below. In other words, in the compound represented by the formula (16),it is preferable that m is 1 and one of four R₃₂ is a carbazolyl group.

In the formula (17), L₂ represents the same as L₂ of the formula (1).

In the formula (17), X₁₁ to X₁₅ each independently represent the same asX₁₁ to X₁₅ of the formula (12).

In the formula (17), R₃₁ to R₃₄ each independently represent the same asR₈ described above. Adjacent ones of R₃₁ may form a ring. Adjacent onesof R₃₂ may form a ring. Adjacent ones of R₃₃ may form a ring. Adjacentones of R₃₄ may form a ring.

In the formula (17): q and r are 4; s is 3; and t is 4.

In the formula (17), Ar represents a substituted or unsubstituted arylgroup having 6 to 30 ring carbon atoms, or a substituted orunsubstituted heterocyclic group having 5 to 30 ring atoms. Note that Armay be bonded to a nitrogen atom of a carbazole skeleton through alinking group without being directly bonded thereto. The linking groupthat links Ar with the nitrogen atom of the carbazole skeletonrepresents the same as L₁ described above. Ar is a substituted orunsubstituted aryl group having 6 to 30 ring carbon atoms. Ar ispreferably a phenyl group, biphenyl group, terphenyl group, naphthylgroup, phenanthryl group, triphenylyl group, dibenzofuranyl group,dibenzothiophenyl group, carbazolyl group and the like. When Ar is asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, Ar is preferably directly bonded to the nitrogen atom of thecarbazole skeleton without the linking group.

In the thermally activated delayed fluorescence compound usable in thefirst exemplary embodiment, as represented by the formula (17), theelectron accepting moiety represented by the formula (10) preferably hasa biscarbazole structure. When the moiety represented by the formula(10) has a mono-carbazole structure consisting of a single carbazoleskeleton, it is speculated that an electron donating performance of themono-carbazole structure is less than that of the amine structure. In acompound in which an azine ring is bonded to the mono-carbazolestructure directly or via a linking group, it is speculated that anelectron accepting performance of the azine ring cannot be canceled bythe electron donating performance of the mono-carbazole structure.Accordingly, such a compound in which the azine ring is bonded to themono-carbazole structure directly or via a linking group is an electronaccepting compound. On the other hand, in a compound in which asubstituent is bonded to the carbazole skeleton, it is considered thatthe electron donating performance is improved. The above biscarbazolestructure is preferable since the electron donating performance isimprovable. In the compound represented by the formula (17) in which theazine ring is bonded to the biscarbazole structure via the linkinggroup, it is speculated that the electron accepting performance of theazine ring and the electron donating performance of the biscarbazolestructure are balanced with each other, thereby decreasing ΔST.

In the first exemplary embodiment, the compound represented by theformula (17) is preferably a compound represented by a formula (18)below.

In the formula (18), L₂ represents the same as L₂ of the formula (1).

In the formula (18), X₁₁ to X₁₅ each independently represent the same asX₁₁ to X₁₅ of the formula (12).

In the formula (18), R₃₁ to R₃₄ each independently represent the same asR₈ described above. Adjacent ones of R₃₁ may form a ring. Adjacent onesof R₃₂ may form a ring. Adjacent ones of R₃₃ may form a ring. Adjacentones of R₃₄ may form a ring.

In the formula (18), q, r, s and t respectively represent the same as q,r, s and t of the formula (17).

In the formula (18), Ar represents the same as Ar of the formula (17).

In the first exemplary embodiment, the compound represented by theformula (17) is preferably a compound represented by a formula (19)below.

In the formula (19), L₂ represents the same as L₂ of the formula (1).

In the formula (19), X₁₁ to X₁₅ each independently represent the same asX₁₁ to X₁₅ of the formula (12).

In the formula (19), R₃₁ to R₃₄ each independently represent the same asR₈ described above. Adjacent ones of R₃₁ may form a ring. Adjacent onesof R₃₂ may form a ring. Adjacent ones of R₃₃ may form a ring. Adjacentones of R₃₄ may form a ring.

In the formula (19), q, r, s and t respectively represent the same as q,r, s and t of the formula (17).

In the formula (19), Ar represents the same as Ar of the formula (17).

In the first exemplary embodiment, in the group represented by theformula (10), it is preferable that the cyclic structure A is asubstituted or unsubstituted benzene ring and the cyclic structure B isa cyclic structure in which any ones of a plurality of five-memberedrings and six-membered rings are mutually fused. In this arrangement,any one of the cyclic structures may have a substituent. In the firstexemplary embodiment, the compound represented by the formula (1) ispreferably a compound represented by a formula (31) below.

In the formula (31), L₂ represents the same as L₂ of the formula (1).

In the formula (31), X₁₁ to X₁₅ each independently represent the same asX₁₁ to X₁₅ of the formula (12).

In the formula (31), R₄₁ and R₄₄ each independently represent the sameas R₈ described above. Adjacent ones of R₄₁ may form a ring. Adjacentones of R₄₄ may form a ring.

In the formula (31), u and v are 4.

In the formula (31), C represents a cyclic structure represented by aformula (32) below and D represents a cyclic structure represented by aformula (33) below. Each of the cyclic structure C and the cyclicstructure D is fused to an adjacent cyclic structure at any position.

In the formula (31), w is an integer of 1 to 4. w is a repeating unit ofa linking cyclic structure in which the cyclic structure C and thecyclic structure D are fused.

In the formula (32), R₄₂ and R₄₃ each independently represent the sameas R₈ of the formula (1). When R₄₂ and R₄₃ are substituents at adjacentpositions, R₄₂ and R₄₃ may form a ring.

In the formula (33), Y₁ represents CR₄₅R₄₆, NR₄₇, a sulfur atom, or anoxygen atom. R₄₅ to R₄₇ each independently represent the same as R₈ inthe formula (1).

In the thermally activated delayed fluorescence compound usable in thefirst exemplary embodiment, as represented by the formula (31), theelectron accepting moiety represented by the formula (10) is anindolocarbazole skeleton or a skeleton in which an indole ring isfurther fused to an indolocarbazole ring. Since the electron acceptingmoiety represented by the formula (10) is provided by such an electrondonating moiety, the electron donating performance of the host materialin this arrangement can be improved more than that of the abovemono-carbazole structure. In the compound represented by the formula(31), it is speculated that the electron accepting performance of theazine ring and the electron donating performance of the electrondonating moiety of the indolocarbazole skeleton and the like arebalanced with each other, thereby decreasing ΔST.

In the formula (31), w is preferably 1. In this arrangement, thecompound represented by the formula (31) is represented by a formula(31a) below.

In the formula (31a), L₂ represents the same as L₂ of the formula (1).

In the formula (31a), X₁₁ to X₁₅ each independently represent the sameas X₁₁ to X₁₅ of the formula (12).

In the formula (31a), R₄₁ and R₄₄ each independently represent the sameas R₈ described above. Adjacent ones of R₄₁ may form a ring. Adjacentones of R₄₄ may form a ring.

In the formula (31a), u and v are 4.

In the formula (31a), C represents a cyclic structure represented by theformula (32) and D represents a cyclic structure represented by theformula (33). Each of the cyclic structure C and the cyclic structure Dis fused to an adjacent cyclic structure at any position.

In the first exemplary embodiment, Cz represented by the formula (1) ispreferably a group selected from the group consisting of groupsrepresented by formulae (110) to (115) below.

In the formulae (110) to (115), Y₂ represents CR₄₈R₄₉, NR₅₀, a sulfuratom, or an oxygen atom. R₄₈ to R₅₀ each independently represent thesame as R₁ to R₇ in the formula (1). The groups represented by theformulae (110) to (115) may further have a substituent.

In the formulae (110) to (115), Y₂ is preferably an oxygen atom.

The compounds including the groups represented by the formulae (110) to(115) are preferably compounds represented by the formulae (31b) to(31g).

In the formulae (31b) to (31g), L₂ represents the same as L₂ of theformula (1).

In the formulae (31b) to (31g), X₁₁ to X₁₅ each independently representthe same as X₁₁ to X₁₅ of the formula (12).

In the formulae (31b) to (31 g), Y₂ represents CR₄₈R₄₉, NR₅₀, a sulfuratom, or an oxygen atom. R₄₈ to R₅₀ each independently represent thesame as R₁ to R₇ in the formula (1).

In the formulae (31 b) to (31 g), Y₂ is preferably an oxygen atom.

In the organic electroluminescence device in the first exemplaryembodiment, Cz of the formula (1) may be a group selected from the groupconsisting of groups derived from structures represented by formulae(116) to (119) below.

In the formulae (116) to (119), Y₂, Y₄ and Y₅ each independentlyrepresent CR₄₈R₄₉, NR₅₀, a sulfur atom, or an oxygen atom. R₄₈ to R₅₀each independently represent the same as R₁ to R₁₆ in the formula (1).The group derived from the structure represented by the formulae (116)to (119) has a hand(s) at any positions and is bonded to L₂ in theformula (1). The groups derived from the structures represented by theformulae (116) to (119) may further have a substituent.

In the exemplary embodiment, when L₂ is a divalent linking group, L₂ ispreferably a substituted or unsubstituted divalent aromatic hydrocarbongroup.

Moreover, in the exemplary embodiment, when L₂ is a divalent linkinggroup, L₂ preferably has a divalent six-membered ring structure, morepreferably a divalent six-membered ring structure represented by aformula (3), (3a) or (3b) below, further preferably a divalentsix-membered ring structure represented by the formula (3) below.

In the formulae (3), (3a) and (3b), X₃₁ to X₃₄ each independentlyrepresent CR₅₁ or a nitrogen atom. R₅₁ each independently represents thesame as R₈ in the formula (1). In the exemplary embodiment, X₃₁ to X₃₄are each independently preferably CR₅₁, in which R₅₁ is more preferablya hydrogen atom, alkyl group, alkoxy group, aryloxy group, cyano group,halogen atom and silyl group.

In the first exemplary embodiment, the compound represented by theformula (1) is preferably a compound represented by a formula (40)below.

In the formula (40), X₁ to X₅ each independently represent CR₁ or anitrogen atom and at least one of X₁ to X₅ is a nitrogen atom.

In the formula (40), one to three of X₁ to X₅ are preferably nitrogenatoms. In the formula (40), adjacent ones of R₁ as the substituents forcarbon atoms may be bonded to each other to form a cyclic structure.

When a single nitrogen atom is provided, X₁ or X₅ is preferably anitrogen atom. When two nitrogen atoms are provided, X₁ and X₅ arepreferably nitrogen atoms. When three nitrogen atoms are provided, X₁,X₃ and X₅ are preferably nitrogen atoms. Among the above arrangements, atriazine ring in which X₁, X₃ and X₅ are nitrogen atoms is preferable inthe formula (40).

In the formula (40), L₁ represents a substituted or unsubstituteddivalent aromatic hydrocarbon group.

In the formula (40), R₁ and R₄₁ to R₄₈ each independently represents ahydrogen atom or a substituent. The substituent in R₁ and R₄₁ to R₄₈ isselected from the group consisting of a cyano group, a substituted orunsubstituted aryl group having 6 to 30 ring carbon atoms, a substitutedor unsubstituted heterocyclic group having 5 to 30 ring atoms, asubstituted or unsubstituted alkyl group having 1 to 30 carbon atoms, asubstituted or unsubstituted alkylsilyl group having 3 to 30 carbonatoms, a substituted or unsubstituted arylsilyl group having 6 to 60ring carbon atoms, a substituted or unsubstituted alkoxy group having 1to 30 carbon atoms, a substituted or unsubstituted aryloxy group having6 to 30 ring carbon atoms, a substituted or unsubstituted alkylaminogroup having 2 to 30 carbon atoms, a substituted or unsubstitutedarylamino group having 6 to 60 ring carbon atoms, a substituted orunsubstituted alkylthio group having 1 to 30 carbon atoms, and asubstituted or unsubstituted arylthio group having 6 to 30 ring carbonatoms.

Each of pairs of R₄₁ and R₄₂, R₄₂ and R₄₃, R₄₃ and R₄₄, R₄₅ and R₄₆, R₄₆and R₄₇, and R₄₇ and R₄₈ may be mutually bonded to form a cyclicstructure.

In the formula (40), G and H each independently represent a cyclicstructure represented by a formula (3g) below or a cyclic structurerepresented by a formula (3h) below. Each of the cyclic structure G andthe cyclic structure H is fused to an adjacent cyclic structure at anyposition.

px and py are each independently an integer of 0 to 4 and respectivelyrepresent the number of the cyclic structure G and the number of thecyclic structure H. When px is an integer of 2 to 4, a plurality ofcyclic structures G may be mutually the same or different. When py is aninteger of 2 to 4, a plurality of cyclic structures H may be mutuallythe same or different. Accordingly, for instance, when px is 2, thecyclic structures G may be either two cyclic structures represented bythe formula (3g) below or two cyclic structures represented by theformula (3h), or alternatively, the cyclic structures G may be acombination of one cyclic structure represented by the formula (3g) andone cyclic structure represented by the formula (3h).

In the formula (3g), R₂₀ and R₂₁ each independently represent the sameas R₁ described above and may be mutually bonded to form a cyclicstructure. R₂₀ and R₂₁ are respectively bonded to carbon atoms formingthe six-membered ring of the formula (3g).

In the formula (3h), Z₈ represents CR₂₂R₂₃, NR₂₄, a sulfur atom, or anoxygen atom. R₂₂ to R₂₄ each independently represent a cyano group, asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, a substituted or unsubstituted heterocyclic group having 5 to 30ring atoms, a substituted or unsubstituted alkyl group having 1 to 30carbon atoms, a substituted or unsubstituted alkylsilyl group having 3to 30 carbon atoms, a substituted or unsubstituted arylsilyl grouphaving 6 to 60 ring carbon atoms, a substituted or unsubstituted alkoxygroup having 1 to 30 carbon atoms, a substituted or unsubstitutedaryloxy group having 6 to 30 ring carbon atoms, a substituted orunsubstituted alkylamino group having 2 to 30 carbon atoms, asubstituted or unsubstituted arylamino group having 6 to 60 ring carbonatoms, a substituted or unsubstituted alkylthio group having 1 to 30carbon atoms; or a substituted or unsubstituted arylthio group having 6to 30 ring carbon atoms. R₂₂ and R₂₃ are each independently preferably asubstituted or unsubstituted alkyl group having 1 to 30 carbon atoms ora substituted or unsubstituted aryl group having 6 to 30 ring carbonatoms. Specific examples of R₂₂ and R₂₃ include a methyl group, ethylgroup, n-propyl group, phenyl group, biphenyl group, and terphenylgroup. R₂₄ is preferably a substituted or unsubstituted aryl grouphaving 6 to 30 ring carbon atoms or a substituted or unsubstitutedheterocyclic group having 5 to 30 ring atoms. Specific examples of R₂₄include a phenyl group, biphenyl group, terphenyl group, naphthyl group,phenanthryl group, triphenylyl group, dibenzofuranyl group,dibenzothiophenyl group, and carbazolyl group. R₂₄ is more preferably asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms. Specific examples of R₂₄ include a phenyl group, biphenyl group,terphenyl group, naphthyl group, phenanthryl group and triphenylylgroup.

In the formula (40), at least one of combinations of substituentsselected from R₄₁ to R₄₈ and R₂₀ to R₂₄ may be mutually bonded to form acyclic structure.

L₁ of the formula (40) preferably has a divalent six-membered ringstructure, more preferably a divalent six-membered ring structurerepresented by a formula (4), (4a) or (4b) below, further preferably adivalent six-membered ring structure represented by the formula (4)below.

In the formulae (4), (4a) and (4b), X₁₁ to X₁₄ each independentlyrepresent CR₁₁ or a nitrogen atom, in which R₁₁ each independentlyrepresents a hydrogen atom or a substituent. The substituent in R₁₁ inthe formulae (4), (4a) and (4b) is selected from the group consisting ofa halogen atom, a cyano group, a substituted or unsubstituted aryl grouphaving 6 to 30 ring carbon atoms, a substituted or unsubstitutedheterocyclic group having 5 to 30 ring atoms, a substituted orunsubstituted alkyl group having 1 to 30 carbon atoms, a substituted orunsubstituted alkylsilyl group having 3 to 30 carbon atoms, asubstituted or unsubstituted arylsilyl group having 6 to 60 ring carbonatoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbonatoms, a substituted or unsubstituted aryloxy group having 6 to 30 ringcarbon atoms, a substituted or unsubstituted alkylamino group having 2to 30 carbon atoms, a substituted or unsubstituted arylamino grouphaving 6 to 60 ring carbon atoms, a substituted or unsubstitutedalkylthio group having 1 to 30 carbon atoms, and a substituted orunsubstituted arylthio group having 6 to 30 ring carbon atoms.

X₁₁ to X₁₄ of the formulae (4), (4a) and (4b) are each independentlypreferably CR₁₁, in which R₁₁ is more preferably a hydrogen atom, alkylgroup, alkoxy group, aryloxy group, cyano group, halogen atom and silylgroup.

Particularly preferably, L₁ is represented by the formula (4); X₁₁ toX₁₄ are each independently CR₁₁; X₁, X₃ and X₅ of the formula (40) arenitrogen atoms; and X₂ and X₄ are CR₁. In other words, the compoundrepresented by the formula (1) is preferably provided by a compound inwhich an electron accepting moiety is a substituted or unsubstitutedtriazine ring and the triazine ring is connected to an electron donatingmoiety by a substituted or unsubstituted p-phenylene group. The compoundin this arrangement is represented by a formula (41) below.

In the formula (41), R₁, R₁₁, R₄₁ to R₄₈, the cyclic structure G, thecyclic structure H, px and py respectively represent the same as R₁,R₁₁, R₄₁ to R₄₈, the cyclic structure G, the cyclic structure H, px andpy described in the formulae (4) and (40).

In the third exemplary embodiment, px and py are preferably the sameinteger, among which px and py are preferably 2. In this arrangement,the formula (40) is represented by a formula (42) below.

In the formula (42), X₁ to X₅, R₄₁ to R₄₈ and L₁ respectivelyindependently represent the same as X₁ to X₅, R₄₁ to R₄₈ and L₁ of theformula (40).

The cyclic structure G₁ and the cyclic structure G₂ each independentlyrepresent the same as the cyclic structure G described above. The cyclicstructure H₁ and the cyclic structure H₂ each independently representthe same as the cyclic structure H described above.

In the formula (42), the cyclic structure G₁ and the cyclic structure H₁are each independently the cyclic structure represented by the formula(3g). The cyclic structure G₂ and the cyclic structure H₂ are eachindependently the cyclic structure represented by the formula (3h).

In the exemplary embodiment, it is also preferable that one of px and pyis 0 while the other of px and py is 4. For instance, when px is 4 andpy is 0, the formula (40) is represented by a formula (43) below.

In the formula (43), X₁ to X₅, R₄₁ to R₄₈ and L₁ respectivelyindependently represent the same as X₁ to X₅, R₄₁ to R₄₈ and L₁ of theformula (40).

The cyclic structure G₁, the cyclic structure G₂, a cyclic structure G₃,and a cyclic structure G₄ each independently represent the same as thecyclic structure G.

In the formula (43), the cyclic structure G₁ and the cyclic structure G₃are each independently the cyclic structure represented by the formula(3g). The cyclic structure G₂ and the cyclic structure G₄ are eachindependently the cyclic structure represented by the formula (3h).

In the formulae (42) and (43), X₁ to X₅ and L₁ are preferably the abovepreferable examples of X₁ to X₅ and L₁.

Herein, the number of carbon atoms forming a ring (also referred to asring carbon atoms) means the number of carbon atoms included in atomsforming the ring itself of a compound in which the atoms are bonded toform the ring (e.g., a monocyclic compound, a fused ring compound, across-linked compound, a carbocyclic compound, and a heterocycliccompound). When the ring is substituted by a substituent, carbon atom(s)included in the substituent is not counted as the ring carbon atoms. Thesame applies to the “ring carbon atoms” described below, unlessparticularly noted. For instance, a benzene ring has 6 ring carbonatoms, a naphthalene ring has 10 ring carbon atoms, a pyridinyl grouphas 5 ring carbon atoms, and a furanyl group has 4 ring carbon atoms.When a benzene ring or a naphthalene ring is substituted, for instance,by an alkyl group, the carbon atoms of the alkyl group are not countedas the ring carbon atoms. For instance, when a fluorene ring (inclusiveof a spirofluorene ring) is bonded as a substituent to a fluorene ring,the carbon atoms of the fluorene ring as a substituent are not countedas the ring carbon atoms.

Herein, the number of atoms forming a ring (also referred to as ringatoms) means the number of atoms forming the ring itself of a compoundin which the atoms are bonded to form the ring (e.g., a monocycliccompound, a fused ring compound, a cross-linked compound, a carbocycliccompound, and a heterocyclic compound). Atom(s) not forming the ring(e.g., hydrogen atom(s) for saturating the valence of the atom whichforms the ring) and atom(s) in a substituent by which the ring issubstituted are not counted as the ring atoms. The same applies to the“ring atoms” described below, unless particularly noted. For instance, apyridine ring has 6 ring atoms, a quinazoline ring has 10 ring atoms,and a furan ring has 5 ring atoms. Hydrogen atoms respectively bonded tocarbon atoms of the pyridine ring or the quinazoline ring and atomsforming a substituent are not counted as the ring atoms. For instance,when a fluorene ring (inclusive of a spirofluorene ring) is bonded as asubstituent to a fluorene ring, the atoms of the fluorene ring as asubstituent are not included in the ring atoms.

Examples of the aryl group having 6 to 30 ring carbon atoms in theexemplary embodiment are a phenyl group, biphenyl group, terphenylgroup, naphthyl group, anthryl group, phenanthryl group, fluorenylgroup, pyrenyl group, chrysenyl group, fluoranthenyl group,benz[a]anthryl group, benzo[c]phenanthryl group, triphenylenyl group,benzo[k]fluoranthenyl group, benzo[g]chrysenyl group,benzo[b]triphenylenyl group, picenyl group, and perylenyl group.

The aryl group in the exemplary embodiment preferably has 6 to 20 ringcarbon atoms, more preferably 6 to 12 ring carbon atoms. Among the arylgroup, a phenyl group, biphenyl group, naphthyl group, phenanthrylgroup, terphenyl group and fluorenyl group are particularly preferable.In a 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group and4-fluorenyl group, a carbon atom at a position 9 is preferablysubstituted by the substituted or unsubstituted alkyl group having 1 to30 carbon atoms in a later-described exemplary embodiment.

Examples of the heterocyclic group having 5 to 30 ring atoms in theexemplary embodiment are a pyridyl group, pyrimidinyl group, pyrazinylgroup, pyridazynyl group, triazinyl group, quinolyl group, isoquinolinylgroup, naphthyridinyl group, phthalazinyl group, quinoxalinyl group,quinazolinyl group, phenanthridinyl group, acridinyl group,phenanthrolinyl group, pyrrolyl group, imidazolyl group, pyrazolylgroup, triazolyl group, tetrazolyl group, indolyl group, benzimidazolylgroup, indazolyl group, imidazopyridinyl group, benzotriazolyl group,carbazolyl group, furyl group, thienyl group, oxazolyl group, thiazolylgroup, isoxazolyl group, isothiazolyl group, oxadiazolyl group,thiadiazolyl group, benzofuranyl group, benzothiophenyl group,benzoxazolyl group, benzothiazolyl group, benzisoxazolyl group,benzisothiazolyl group, benzoxadiazolyl group, benzothiadiazolyl group,dibenzofuranyl group, dibenzothiophenyl group, piperidinyl group,pyrrolidinyl group, piperazinyl group, morpholyl group, phenazinylgroup, phenothiazinyl group, and phenoxazinyl group.

The heterocyclic group in the exemplary embodiment preferably has 5 to20 ring atoms, more preferably 5 to 14 ring atoms. Among the above, a1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group,4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenylgroup, 3-dibenzothiophenyl group, 4-dibenzothiophenyl group,1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolylgroup, and 9-carbazolyl group are particularly preferable. A nitrogenatom at a position 9 of each of 1-carbazolyl group, 2-carbazolyl group,3-carbazolyl group and 4-carbazolyl group is preferably substituted by asubstituted or unsubstituted aryl group having 6 to 30 ring carbon atomsor a substituted or unsubstituted heterocyclic group having 5 to 30 ringatoms in the exemplary embodiment.

The alkyl group having 1 to 30 carbon atoms in the exemplary embodimentmay be linear, branched or cyclic. Examples of the linear or branchedalkyl group are a methyl group, ethyl group, propyl group, isopropylgroup, n-butyl group, s-butyl group, isobutyl group, t-butyl group,n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonylgroup, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecylgroup, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group,n-heptadecyl group, n-octadecyl group, neo-pentyl group, amyl group,isoamyl group, 1-methylpentyl group, 2-methylpentyl group, 1-pentylhexylgroup, 1-butylpentyl group, 1-heptyloctyl group and 3-methylpentylgroup.

The linear or branched alkyl group in the exemplary embodimentpreferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbonatoms. Among the linear or branched alkyl group, a methyl group, ethylgroup, propyl group, isopropyl group, n-butyl group, s-butyl group,isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, amylgroup, isoamyl group and neopentyl group are particularly preferable.

Examples of the cycloalkyl group in the exemplary embodiment are acyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexylgroup, 4-metylcyclohexyl group, adamantyl group and norbornyl group. Thecycloalkyl group preferably has 3 to 10 ring carbon atoms, morepreferably 5 to 8 ring carbon atoms. Among the cycloalkyl group, acyclopentyl group and a cyclohexyl group are particularly preferable.

A halogenated alkyl group provided by substituting an alkyl group with ahalogen atom is exemplified by one provided by substituting an alkylgroup having 1 to 30 carbon atoms with one or more halogen groups.Specific examples of the above halogenated alkyl group are afluoromethyl group, difluoromethyl group, trifluoromethyl group,fluoroethyl group, trifluoromethylmethyl group, trifluoroethyl group andpentafluoroethyl group.

The alkylsilyl group having 3 to 30 carbon atoms in the exemplaryembodiment is exemplified by a trialkylsilyl group having the aboveexamples of the allyl group having 1 to 30 carbon atoms. Specificexamples of the alkylsilyl group are a trimethylsilyl group,triethylsilyl group, tri-n-butylsilyl group, tri-n-octylsilyl group,triisobutylsilyl group, dimethylethylsilyl group, dimethylisopropylsilylgroup, dimethyl-n-propylsilyl group, dimethyl-n-butylsilyl group,dimethyl-t-butylsilyl group, diethylisopropylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, and triisopropylsilylgroup. Three alkyl groups in the trialkylsilyl group may be the same ordifferent.

Examples of the arylsilyl group having 6 to 30 ring carbon atoms in theexemplary embodiment are a dialkylarylsilyl group, alkyldiarylsilylgroup and triarylsilyl group.

The dialkylarylsilyl group is exemplified by a dialkylarylsilyl groupincluding two of the alkyl group listed as the examples of the alkylgroup having 1 to 30 carbon atoms and one of the aryl group listed asthe examples of the aryl group having 6 to 30 ring carbon atoms. Thedialkylarylsilyl group preferably has 8 to 30 carbon atoms.

The alkyldiarylsilyl group is exemplified by an alkyldiarylsilyl groupincluding one of the alkyl group listed as the examples of the alkylgroup having 1 to 30 carbon atoms and two of the aryl group listed asthe examples of the aryl group having 6 to 30 ring carbon atoms. Thealkyldiarylsilyl group preferably has 13 to 30 carbon atoms.

The triarylsilyl group is exemplified by a triarylsilyl group includingthree of the aryl group listed as the examples of the aryl group having6 to 30 ring carbon atoms. The triarylsilyl group preferably has 18 to30 carbon atoms.

The alkoxy group having 1 to 30 carbon atoms in the exemplary embodimentis represented by —OZ₁. Z₁ is exemplified by the above alkyl grouphaving 1 to 30 carbon atoms. Examples of the alkoxy group are a methoxygroup, ethoxy group, propoxy group, butoxy group, pentyloxy group andhexyloxy group.

A halogenated alkoxy group provided by substituting an alkoxy group witha halogen atom is exemplified by one provided by substituting an alkoxygroup having 1 to 30 carbon atoms with one or more halogen groups.

The aryloxy group having 6 to 30 ring carbon atoms in the exemplaryembodiment is represented by —OZ₂. Z₂ is exemplified by the aryl grouphaving 6 to 30 ring carbon atoms or a monocyclic group and a fusedcyclic group described below. The aryloxy group is exemplified by aphenoxy group.

The alkylamino group having 2 to 30 carbon atoms is represented by—NHR_(V) or —N(R_(V))₂. R_(V) is exemplified by the alkyl group having 1to 30 carbon atoms.

The arylamino group having 6 to 60 ring carbon atoms is represented by—NHR_(W) or —N(R_(W))₂. R_(W) is exemplified by the above aryl grouphaving 6 to 30 ring carbon atoms.

The alkylthio group having 1 to 30 carbon atoms is represented by—SR_(V). R_(V) is exemplified by the alkyl group having 1 to 30 carbonatoms.

The arylthio group having 6 to 30 ring carbon atoms is represented by—SR_(W). R_(W) is exemplified by the above aryl group having 6 to 30ring carbon atoms.

In the invention, “carbon atoms forming a ring (ring carbon atoms)” meancarbon atoms forming a saturated ring, an unsaturated ring, or anaromatic ring. “Atoms forming a ring (ring atoms)” mean carbon atoms andhetero atoms forming a hetero ring including a saturated ring,unsaturated ring, or aromatic ring.

In the invention, a hydrogen atom includes isotope having differentnumbers of neutrons, specifically, protium, deuterium and tritium.

In the exemplary embodiment, examples of the substituent meant by“substituted or unsubstituted” and the substituent in the cyclicstructures A, B, C, D, G and H are an alkenyl group, alkynyl group,aralkyl group, halogen atom, cyano group, hydroxyl group, nitro groupand carboxy group, in addition to the above-described aryl group,heterocyclic group, alkyl group (linear or branched alkyl group,cycloalkyl group and haloalkyl group), alkylsilyl group, arylsilylgroup, alkoxy group, aryloxy group, alkylamino group, arylamino group,alkylthio group, and arylthio group.

Among the above substituents, an aryl group, heterocyclic group, alkylgroup, halogen atom, alkylsilyl group, arylsilyl group and cyano groupare preferable. More preferable substituents are one listed as thepreferable substituents described for each substituent.

In the exemplary embodiment, the aromatic hydrocarbon group ispreferably an aryl group having 6 to 30 ring atoms and the heterocyclicgroup is preferably a heterocyclic group having 5 to 30 ring atoms.

The alkenyl group is preferably an alkenyl group having 2 to 30 carbonatoms, which may be linear, branched or cyclic. Examples of the alkenylgroup include a vinyl group, propenyl group, butenyl group, oleyl group,eicosapentaenyl group, docosahexaenyl group, styryl group,2,2-diphenylvinyl group, 1,2,2-triphenylvinyl group, 2-phenyl-2-propenylgroup, cyclopentadienyl group, cyclopentenyl group, cyclohexenyl group,and cyclohexadienyl group.

The alkynyl group is preferably an alkynyl group having 2 to 30 carbonatoms, which may be linear, branched or cyclic. Examples of the alkynylgroup include ethynyl, propynyl, and 2-phenylethynyl.

The aralkyl group is preferably an aralkyl group having 6 to 30 ringcarbon atoms and is represented by —Z₃—Z₄. Z₃ is exemplified by analkylene group corresponding to the above alkyl group having 1 to 30carbon atoms. Z₄ is exemplified by the above aryl group having 6 to 30ring carbon atoms. The aralkyl group is preferably an aralkyl grouphaving 7 to 30 carbon atoms, in which an aryl portion has 6 to 30 carbonatoms, preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbonatoms, and an alkyl portion has 1 to 30 carbon atoms, preferably 1 to 20carbon atoms, more preferably 1 to 10 carbon atoms, further preferably 1to 6 carbon atoms. Examples of the aralkyl group are a benzyl group,2-phenylpropane-2-yl group, 1-phenylethyl group, 2-phenylethyl group,1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group,α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethylgroup, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group,β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethylgroup, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.

Examples of the halogen atom are fluorine, chlorine, bromine and iodine,among which a fluorine atom is preferable.

“Unsubstituted” in “substituted or unsubstituted” means that a group isnot substituted by the above-described substituents but bonded with ahydrogen atom.

Herein, “XX to YY carbon atoms” in the description of “substituted orunsubstituted ZZ group having XX to YY carbon atoms” represent carbonatoms of an unsubstituted ZZ group and do not include carbon atoms of asubstituent(s) of a substituted ZZ group. “YY” is larger than “XX” andeach of “XX” and “YY” represents an integer of 1 or more.

Herein, “XX to YY atoms” in the description of “substituted orunsubstituted ZZ group having XX to YY atoms” represent atoms of anunsubstituted ZZ group and does not include atoms of a substituent(s) ofa substituted ZZ group. “YY” is larger than “XX” and each of “XX” and“YY” represents an integer of 1 or more.

The same description as the above applies to “substituted orunsubstituted” in the following compound or a partial structure thereof.

Specific examples of the compound represented by the formula (1) areshown below, but the compound represented by the formula (4) is notlimited thereto.

The compound represented by the formula (1) can be synthesized by aknown synthetic method.

A film thickness of the emitting layer is preferably in a range of 5 nmto 50 nm, more preferably in a range of 7 nm to 50 nm and mostpreferably in a range of 10 nm to 50 nm. The thickness of less than 5 nmmay cause difficulty in forming the emitting layer and in controllingchromaticity, while the thickness of more than 50 nm may raise drivevoltage.

Substrate

The organic EL device according to the exemplary embodiment is formed ona light-transmissive substrate. The light-transmissive substrate, whichsupports the anode, the organic compound layer and the cathode formingthe organic EL device, is preferably a smooth and flat substrate thattransmits 50% or more of light in a visible region of 400 nm to 700 nm.

The light-transmissive plate is exemplarily a glass plate, a polymerplate or the like.

The glass plate is formed of soda-lime glass,barium/strontium-containing glass, lead glass, aluminosilicate glass,borosilicate glass, barium borosilicate glass, quartz and the like.

The polymer plate is formed of polycarbonate, acryl, polyethyleneterephthalate, polyether sulfide and polysulfone.

Anode and Cathode

The anode of the organic EL device injects holes into the emittinglayer, so that it is efficient that the anode has a work function of 4.5eV or more.

Exemplary materials for the anode are indium-tin oxide (ITO), tin oxide(NESA), indium zinc oxide, gold, silver, platinum and copper.

When light from the emitting layer is to be emitted through the anode,the anode preferably transmits more than 10% of the light in the visibleregion. Sheet resistance of the anode is preferably several hundredsΩ/sq. or lower. The thickness of the anode is typically in the range of10 nm to 1 m, and preferably in the range of 10 nm to 200 nm, though itdepends on the material of the anode.

The cathode is preferably formed of a material with smaller workfunction in order to inject electrons into the emitting layer.

Although a material for the cathode is subject to no specificlimitation, examples of the material are indium, aluminum, magnesium,alloy of magnesium and indium, alloy of magnesium and aluminum, alloy ofaluminum and lithium, alloy of aluminum, scandium and lithium, and alloyof magnesium and silver.

Like the anode, the cathode may be made by forming a thin film on, forinstance, the electron transporting layer and the electron injectinglayer by a method such as vapor deposition. In addition, the light fromthe emitting layer may be emitted through the cathode. When light fromthe emitting layer is to be emitted through the cathode, the cathodepreferably transmits more than 10% of the light in the visible region.Sheet resistance of the cathode is preferably several hundreds Ω/sq. orlower. The thickness of the cathode is typically in the range of 10 nmto 1 m, and preferably in the range of 50 nm to 200 nm, though itdepends on the material of the cathode.

Hole Injecting-Transporting Layer

The hole injection/transport layer helps injection of holes to theemitting layer and transport the holes to an emitting region. A compoundhaving a large hole mobility and a small ionization energy is used asthe hole injection/transport layer.

A material for forming the hole injecting layer and the holetransporting layer is preferably a material for transporting the holesto the emitting layer at a lower electric field intensity. For instance,an aromatic amine compound is preferably used. A material for the holeinjecting layer is preferably a porphyrin compound, an aromatic tertiaryamine compound or a styryl amine compound, particularly preferably thearomatic tertiary amine compound such as hexacyanohexaazatriphenylene(HAT).

Electron Injecting-Transporting Layer

The electron injecting-transporting layer helps injection of theelectrons into the emitting layer and transports the electrons to anemitting region. A compound having a large electron mobility is used asthe electron injecting-transporting layer.

A preferable example of the compound used as the electroninjecting-transporting layer is an aromatic heterocyclic compound havingat least one heteroatom in a molecule. Particularly, anitrogen-containing cyclic derivative is preferable. Thenitrogen-containing cyclic derivative is preferably a heterocycliccompound having a nitrogen-containing six-membered or five-membered ringskeleton, or a fused aromatic cyclic compound having anitrogen-containing six-membered or five-membered ring skeleton.Moreover, the electron injecting⋅transporting layer may contain analkali metal and the like

In the organic EL device in the exemplary embodiment, in addition to theaforementioned compounds, any compound selected from compounds to beused in a typical organic El device is usable as a compound for theorganic compound layer other than the emitting layer.

Layer Formation Method(s)

A method for forming each layer of the organic EL device in theexemplary embodiment is subject to no limitation except for the aboveparticular description. However, known methods of dry film-forming suchas vacuum deposition, sputtering, plasma or ion plating and wetfilm-forming such as spin coating, dipping, flow coating or ink-jet areapplicable.

Thickness

The thickness of each organic layer of the organic EL device in theexemplary embodiment is subject to no limitation except for thethickness particularly described above. However, the thickness istypically preferably in a range of several nanometers to 1 μm because anexcessively thin film is likely to entail defects such as a pin holewhile an excessively thick film requires high applied voltage anddeteriorates efficiency.

Second Exemplary Embodiment

An organic EL device according to a second exemplary embodiment will bedescribed below. In the description of the second exemplary embodiment,the same components as those in the first exemplary embodiment aredenoted by the same reference signs and names to simplify or omit anexplanation of the components. In the second exemplary embodiment, thesame materials and compounds as described in the first exemplaryembodiment are usable for a material and a compound which are notparticularly described.

The organic EL device in the second exemplary embodiment has the samedevice arrangement as in the first exemplary embodiment, in which thecompounds contained in the emitting layer are different. The organic ELdevice 1 in the second exemplary embodiment contains the first andsecond compounds according to the first exemplary embodiment and a thirdcompound in the emitting layer. The third compound is also a compoundemitting thermally activated delayed fluorescence. Also in the secondexemplary embodiment, it is preferable to use the materials used in theabove exemplary embodiment.

In the second exemplary embodiment, a concentration of the thirdcompound in the emitting layer is preferably 20 mass % or more. It ispreferable that the concentration of the first compound is 20 mass % ormore, the concentration of the second compound is 20 mass % or more andthe concentration of the third compound is 20 mass % or more in theemitting layer. A total concentration of the first compound, the secondcompound and the third compound in the emitting layer is 100 mass % orless.

In the second exemplary embodiment, it is preferable that a differencebetween the singlet energy EgS(M1) of the first compound and singletenergy EgS(M3) of the third compound is 0.2 eV or less and a differencebetween the singlet energy EgS(M2) of the second compound and thesinglet energy EgS(M3) of the third compound is 0.2 eV or less. In otherwords, it is preferable to satisfy a relationship of|EgS(M1)−EgS(M3)|≤0.2 eV and a relationship of |EgS(M2)−EgS(M3)|≤0.2 eV.

Moreover, in the second exemplary embodiment, it is preferable that adifference between energy gap Eg_(77K)(M1) at 77K of the first compoundand energy gap Eg_(77K)(M3) at 77K of the third compound is 0.2 eV orless and a difference between energy gap Eg_(77K)(M2) at 77K of thesecond compound and the energy gap Eg_(77K)(M3) at 77K of the thirdcompound is 0.2 eV or less. In other words, it is preferable to satisfya relationship of |Eg_(77K)(M1)−Eg_(77K)(M3)|≤0.2 eV and a relationshipof |Eg_(77K)(M2)−Eg_(77K)(M3)|≤0.2 eV.

In the second exemplary embodiment, at least one of a plurality of thethermally activated delayed fluorescence compounds contained in theemitting layer is preferably a compound in which a difference ΔSTbetween singlet energy EgS and energy gap Eg_(77K) at 77K satisfies arelationship represented by a numerical formula (1) below.

ΔST=EgS−Eg _(77K)<0.3 (eV)  (Numerical Formula 1)

In the second exemplary embodiment, the first compound, the secondcompound and the third compound which are thermally activated delayedfluorescence compounds are contained in the emitting layer. Furtheralternatively, the first compound is preferably a compound satisfyingthe relationship represented by the numerical formula (1-1).Alternatively, the second compound is preferably a compound satisfyingthe relationship represented by the numerical formula (1-2). Stillfurther alternatively, the third compound is preferably a compound inwhich a difference ΔST(M3) between the singlet energy EgS(M3) and theenergy gap Eg_(77K)(M3) at 77K satisfies a relationship represented by anumerical formula (1-3) below. The third compound is more preferably acompound in which ΔST(M3) is less than 0.2 eV.

ΔST(M3)=EgS(M3)−Eg _(77K)(M3)<0.3 eV  (Numerical Formula 1-3)

It is further preferable that the first compound satisfies therelationship of the numerical formula (1-1), the second compoundsatisfies the relationship of the numerical formula (1-2), and the thirdcompound satisfies the relationship of the numerical formula (1-3).

The organic EL device of the second exemplary embodiment can also reducethe drive voltage and prolong the emission lifetime in the same manneras in the first exemplary embodiment.

Third Exemplary Embodiment

An organic EL device according to a third exemplary embodiment will bedescribed below. In the description of the second exemplary embodiment,the same components as those in the first exemplary embodiment aredenoted by the same reference signs and names to simplify or omit anexplanation of the components. In the third exemplary embodiment, thesame materials and compounds as described in the above exemplaryembodiments are usable for a material and a compound which are notparticularly described.

The thermally activated delayed fluorescence compound is exemplified bya compound represented by a formula (2) below. In the third exemplaryembodiment, one of the thermally activated delayed fluorescencecompounds contained in the emitting layer is represented by the formula(2) below. The compound represented by the formula (1) described in theabove exemplary embodiments may also be used as the thermally activateddelayed fluorescence compound.

In the formula (2), L₂₀ represents a substituted or unsubstituted(a+g)-valent aromatic hydrocarbon group or a substituted orunsubstituted (a+g)-valent heterocyclic group.

In the formula (2), L₂₀₁ represents a substituted or unsubstituteddivalent aromatic hydrocarbon group or a substituted or unsubstituteddivalent heterocyclic group.

In the formula (2), a is an integer of 1 to 6 and b is an integer of 1to 6. a and b are each independently preferably an integer of 1 to 3,more preferably 1 or 2. When a is 2 or more, HAr to be bonded to L₂₀ is2 or more, in which HAr may be mutually the same or different.

In the formula (2), g is an integer of 0 to 2, in which g is preferably0 or 1. When g is from 1 to 2, L₂₀ and L₂₀₁ may be mutually the same ordifferent. When g is 2, two L₂₀₁ may be mutually the same or different.

In the formula (2), HAr is a group derived from a structure representedby a formula (20) below.

In the formula (20), X₂₀ represents a single bond, an oxygen atom, asulfur atom, a carbonyl group, NR₉, CR₁₀R₁₁, SiR₁₂R₁₃ or GeR₁₄R₁₅. R₉ toR₁₅ each independently represent the same as R₁ to R₇ described above.In the formula (20), X₂₀ preferably represents an oxygen atom, a sulfuratom, a carbonyl group, NR₉, CR₁₀R₁₁, SiR₁₂R₁₃ or GeR₁₄R₁₅.

A cyclic structure represented by the formula (20) is selected from thegroup consisting of cyclic structures represented by formulae (20b) to(20i).

In the formulae (20), (20b) to (20i), G and H each independentlyrepresent a substituted or unsubstituted cyclic structure. When at leastone of the cyclic structure G and the cyclic structure H have aplurality of substituents, adjacent ones of the substituents may form aring. The ring to be formed may be a saturated or unsaturated ring. Thesubstituent at this time is preferably an electron donating substituent.Moreover, adjacent substituents preferably further form an electrondonating ring. Among the cyclic structures, the cyclic structureselected from the group consisting of cyclic structures represented bythe formulae (20c) to (20i) is preferable.

When at least one of the cyclic structure A and the cyclic structure Bis a substituted or unsubstituted heterocyclic structure in the formulae(20) and (20b) to (20i), the heterocyclic structure has a partialstructure represented by a formula (20-2) below.

The group derived from the structure represented by the formula (20) ispreferably a group represented by formula (20-1) below.

In the formula (20-1), X₂₀ represents the same as X₂₀ in the formula(20). In other words, the group represented by the formula (20-1) is agroup selected from the group consisting of groups represented byformulae (20b-1) to (20i-1) below.

In the formulae (20b-1) to (20i-1), the cyclic structure G and thecyclic structure H respectively represent the same as the cyclicstructure G and the cyclic structure H in the formulae (20) and (20b) to(20i). Among the above groups, the group selected from the groupconsisting of the groups represented by the formulae (20c-1) to (20i-1)is preferable as HAr of the formula (2).

In the third exemplary embodiment, HAr of the formula (2) is preferablya group derived from a structure represented by a formula (2B) below.

In the formula (2B), X₂ represents the same as X₂ of the formula (20).X₂ is preferably an oxygen atom, a sulfur atom, a carbonyl group, NR₉,CR₁₀R₁₁, SiR₁₂R₁₃ or GeR₁₄R₁₅.

In the formula (2B), R₆₁ and R₆₂ each independently represent the sameas R₈ described above. Adjacent ones of R₆₁ may form a ring. Adjacentones of R₆₂ may form a ring.

In the formula (2B), i and j are 4.

In the formula (2B), E represents a cyclic structure represented by aformula (2h) below and F represents a cyclic structure represented by aformula (2i) or (2j) below. Each of the cyclic structure E and thecyclic structure F is fused to an adjacent cyclic structure at anyposition. In the formula (2B), h is an integer of 0 to 4. h is arepeating unit of a linking cyclic structure in which the cyclicstructure E and the cyclic structure F are fused to each other. When his 2 or more, a plurality of cyclic structures F may be the same ordifferent.

In the formula (2h), when R₆₃ and R₆₄ are substituents at adjacentpositions, R₆%3 and R₆₄ may form a ring.

Y₃ in the formula (2i) represents CR₆₅R₆₆, NR₆₇, a sulfur atom, anoxygen atom or a nitrogen atom to be bonded to L₂₀. Y₆ in the formula(2j) represents CR₆₅R₆₆, NR₆₇, or a nitrogen atom to be bonded to L₂₀.

X₄ in the formula (2j) represents NR₉ or CR₁₀R₁₁ in which R₉ to R₁₁ eachindependently represent the same as R₁ to R₇ described above. R %₃ andR₆₄ each independently represent the same as R₈ described above. R % sto R %₇ each independently represent the same as R₁ to R₇ describedabove.

In the exemplary embodiment, h in the formula (2B) is preferably 0 or 1.

In the formula (2B), when h is 0, HAr is preferably a group representedby a formula (2b) or (2bx) below.

In the formulae (2b) and (2bx), X₂ represents a single bond, an oxygenatom, a sulfur atom, a carbonyl group, NR₉, CR₁₀R₁₁, SiR₁₂R₁₃ orGeR₁₄R₁₅. In other words, the group represented by the formula (2b) is agroup selected from the group consisting of groups represented byformulae (2b-1) to (2b-8) below.

In the formulae (2b), (2bx) and (2b-1) to (2b-8), c and d are 4. Amongthe above groups, the group selected from the group consisting of thegroups represented by the formulae (2b-2) to (2b-8) is preferable as HArof the formula (2).

In the formulae (2b), (2bx) and (2b-1) to (2b-8), R₉ to R₁₅ eachindependently represent the same as R₁ to R₇ described above. R₁₇ andR₁₈ each independently represent the same as R₈ described above.Adjacent ones of R₁₇ may form a ring. Adjacent ones of R₁₈ may form aring.

In the formula (2bx), Ar₄ represents the same as R₁ to R₈ describedabove. Ar₄ is preferably a substituted or unsubstituted aryl grouphaving 6 to 30 ring carbon atoms or a substituted or unsubstitutedheterocyclic group having 5 to 30 ring atoms, more preferably asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms. Ar₄ is preferably a phenyl group, biphenyl group, terphenylgroup, naphthyl group, phenanthryl group, triphenylyl group,dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group and thelike.

In the formula (2), Az₂ is represented by a formula (2d) below.

In the formula (2d), X₂₁ to X₂₆ each independently represent CR₁₆ or anitrogen atom. At least one of X₂₁ to X₂₆ is a nitrogen atom and b ofX₂₁ to X₂₆ is a carbon atom to be bonded to L₂₀ or L₂₀₁. Since b is aninteger of 1 to 3 as described above, one to three of X₂₁ to X₂₆ arecarbon atom(s) to be bonded to L₂₀. R₁₆ represents the same as R₈described above.

In the formula (21), one to three of X₂₁ to X₂₆ are preferably nitrogenatom(s). For instance, when X₂₆ is a carbon atom bonded to L₂₀ and oneof X₂₁ to X₂₅ is a nitrogen atom, X₂₁ or X₂ is preferably a nitrogenatom. When two of X₂₁ to X₂₅ are nitrogen atoms, X₂₁ and X₂₅ arepreferably nitrogen atoms. When three of X₂₁ to X₂₅ are nitrogen atoms,X₂₁, X₂₃ and X₂₅ are preferably nitrogen atoms. A triazine ring in whichX₂₁, X₂₃ and X₂₅ are nitrogen atoms is preferable in the formula (2d).

In the exemplary embodiment, it is preferable that a and b are 1 and gis 0 in the formula (2) and X₂₆ is a carbon atom to be bonded to L₂₀ informula (2d). In other words, the compound represented by the formula(2) is preferably a compound represented by a formula (21) below.

In the formula (21), X₂ represents the same as X₂ of the formula (2b).

In the formula (21), L₂₁ represents a substituted or unsubstituteddivalent aromatic hydrocarbon group or a substituted or unsubstituteddivalent heterocyclic group.

In the formula (21), X₂₁ to X₂₅ each independently represent CR₁₆ or anitrogen atom and at least one of X₂₁ to X₂₅ is a nitrogen atom. Whenone of X₂₁ to X₂₅ is a nitrogen atom, X₂₁ or X₂₅ is preferably nitrogenatoms. When two of X₂₁ to X₂₅ are nitrogen atoms, X₂₁ and X₂₅ arepreferably nitrogen atoms. When three of X₂₁ to X₂₅ are nitrogen atoms,X₂₁, X₂₃ and X₂₅ are preferably nitrogen atoms.

In the formula (21), c and d are 4 and R₁₇ and R₁₈ each independentlyrepresent the same as R₈ described above. A plurality of R₁₇ may bemutually the same or different. A plurality of R₁₈ may be mutually thesame or different.

In the third exemplary embodiment, the compound represented by theformula (2) is preferably the compound represented by the formula (21),in which X₂ is preferably an oxygen atom.

In the third exemplary embodiment, it is preferable that a is 2 and b is1 in the formula (2) and X₂₆ is a carbon atom to be bonded to L₂₀ informula (2d). In other words, the compound represented by the formula(2) is preferably a compound represented by a formula (22) below.

In the formula (22), X₂₇ and X₂₈ each independently represent the sameas X₂ of the formula (2b), in which X₂₇ and X₂₈ may be mutually the sameor different.

In the formula (22), L₂₂ is a substituted or unsubstituted trivalentaromatic hydrocarbon group or a substituted or unsubstituted trivalentheterocyclic group.

In the formula (22), X₂₁ to X₂₅ each independently represent CR₁₆ or anitrogen atom and at least one of X₂₁ to X₂₅ is a nitrogen atom. Whenone of X₂₁ to X₂₅ is a nitrogen atom, X₂₁ or X₂₅ is preferably nitrogenatoms. When two of X₂₁ to X₂₅ are nitrogen atoms, X₂₁ and X₂₅ arepreferably nitrogen atoms. When three of X₂₁ to X₂₅ are nitrogen atoms,X₂₁, X₂₃ and X₂₅ are preferably nitrogen atoms.

In the formula (22), c, d, c and f are each 4 and R₁₇ to R₂₀ eachindependently represent the same as R₈ described above. Adjacent ones ofR₁₇ may form a ring. Adjacent ones of R₁₈ may form a ring.

In the third exemplary embodiment, the compound represented by theformula (2) is preferably the compound represented by the formula (22),in which X₂₇ and X₂₈ are preferably oxygen atoms.

In the third exemplary embodiment, it is preferable that a is 1, b is 2,and g is 0 in the formula (2) and X₂₄ and X₂₆ are carbon atoms to bebonded to L₂₀ and X₂₁, X₂₃ and X₂₅ are nitrogen atoms in formula (2d).In other words, the compound represented by the formula (2) ispreferably a compound represented by a formula (23) below.

In the formula (23), X₂₇ and X₂₅ represent the same as X₂ of the formula(2b) and X₂₇ and X₂₈ may be mutually the same or different.

In the formula (23), L₂₃ and L₂₄ each independently represent asubstituted or unsubstituted divalent aromatic hydrocarbon group or asubstituted or unsubstituted divalent heterocyclic group.

In the formula (23), Ar₂ represents the same as R₁ to R₈ describedabove. Ar₂ is preferably a substituted or unsubstituted aryl grouphaving 6 to 30 ring carbon atoms or a substituted or unsubstitutedheterocyclic group having 5 to 30 ring atoms, more preferably asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms. Ar₂ is preferably a phenyl group, biphenyl group, terphenylgroup, naphthyl group, phenanthryl group, triphenylyl group,dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group and thelike.

In the formula (23), c, d, e and f are each 4 and R₁₇ to R₂₀ eachindependently represent the same as R₈ described above. Adjacent ones ofR₁₇ may form a ring. Adjacent ones of R₁₈ may form a ring.

In the third exemplary embodiment, the compound represented by theformula (2) is preferably the compound represented by the formula (23),in which X₂₇ and X₂₈ are preferably oxygen atoms.

In the third exemplary embodiment, in the compound represented by theformula (2), it is preferable that HAr is the group represented by theformula (2b), L₂₀ is a substituted or unsubstituted divalentheterocyclic group, and g is 1. In this arrangement, L₂₀ is morepreferably a substituted or unsubstituted divalent carbazolyl group.Further, the compound represented by the formula (2) is preferably acompound represented by a formula (24) below.

In the formula (24), X₂₁ to X₂₅ represent the same as X₂₁ to X₂₅ of theformula (21).

In the formula (24), R₁₇ to R₁₈ and R₂₃ to R₂₄ each independentlyrepresent the same as R₈ described above. Adjacent ones of R₁₇ may forma ring. Adjacent ones of R₁₈ may form a ring. Adjacent ones of R₂₃ mayform a ring. Adjacent ones of R₂₄ may form a ring.

In the formula (24), L₂₀₁ represents the same as L₂₀₁ of the formula(2).

In the formula (24), c, d and x are 4 and w is 3.

In the formula (2B), when h is 1 and the cyclic structure F isrepresented by the formula (2i), the structure of the formula (2B) isrepresented by formulae (2B-1) to (2B-6) below.

In the formulae (2B-1) to (2B-6), X₂ represents the same as X₂ of theformula (2b).

In the formulae (2B-1) to (2B-6), R₆₁ to R₆ each independently representthe same as R₈ described above. Adjacent ones of R₆₁ may form a ring.Adjacent ones of R₆₂ may form a ring. Adjacent R₆₃ and R₆₄ may form aring.

In the formulae (2B-1) to (2B-6), Y₃ represents the same as Y₃ of theformula (2i).

In the formulae (2B-1) to (2B-6), i and j are 4.

Groups derived from the structure represented by the formulae (2B-1) to(2B-6) are preferably groups represented by formulae (2B-7) to (2B-18)below.

In the formulae (2B-7) to (2B-12), X₂ represents the same as X₂ of theformula (2b), in which X₂ is preferably an oxygen atom.

In the formulae (2B-7) to (2B-12), R₆₁ to R₆₄ each independentlyrepresent the same as R₈ described above. Adjacent ones of R₆₁ may forma ring. Adjacent ones of R₆₂ may form a ring. Adjacent R₆₃ and R₆₄ mayform a ring.

In the formulae (2B-7) to (2B-12), Y₃ represents the same as Y₃ of theformula (2i), among which Y₃ is preferably NR₆₇. R₆₇ represents the sameas R₁ to R₇ described above and is preferably a substituted orunsubstituted aryl group having 6 to 30 ring carbon atoms.

In the formulae (2B-7) to (2B-12), i and j are 4.

In the formulae (2B-13) to (2B-18), X₂ represents the same as X₂ of theformula (2b), in which X₂ is preferably an oxygen atom.

In the formulae (2B-13) to (2B-18), R₆₁ to R₆₄ each independentlyrepresent the same as R₈ described above. Adjacent ones of R₆₁ may forma ring. Adjacent ones of R₆₂ may form a ring. Adjacent R₆₃ and R₆₄ mayform a ring.

In the formulae (2B-13) to (2B-18), Ar₃ represents the same as R₁ to R₇described above. Ar₃ is preferably a substituted or unsubstituted arylgroup having 6 to 30 ring carbon atoms or a substituted or unsubstitutedheterocyclic group having 5 to 30 ring atoms, more preferably asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms. Ar₃ is preferably a phenyl group, biphenyl group, terphenylgroup, naphthyl group, phenanthryl group, triphenylyl group,dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group and thelike.

In the formulae (2B-13) to (2B-18), i and j are 4.

In the formula (2B), when h is 1 and the cyclic structure F isrepresented by the formula (2i), the structure of the formula (2B) isrepresented by formulae (2B-19) to (2B-20) below.

In the formulae (2B-19) to (2B-20), X₂ and X₄ represent the same as X₂of the formula (2b) and X₄ represents the same as X₄ of the formula(2j).

In the formulae (2B-19) to (2B-20), R₆₁ to R₆₄ each independentlyrepresent the same as R₈ described above. Adjacent ones of R₆₁ may forma ring. Adjacent ones of R₆₂ may form a ring. Adjacent R₆₃ and R₆₄ mayform a ring.

In the formulae (2B-19) to (2B-20), Y₆ represents the same as Y₃ of theformula (2i).

In the formulae (2B-19) to (2B-20), i and j are 4.

Groups derived from the structure represented by the formulae (2B-19) to(2B-20) are preferably groups represented by formulae (2B-21) to (2B-22)below.

In the formulae (2B-21) to (2B-22), X₂, X₄, R₆₁ to R₆₄, Y₆, i and jrespectively represent the same as X₂, X₄, R₆₁ to R₆₄, Y₆, i and j ofthe formulae (2B-19) to (2B-20).

In the exemplary embodiment, when L₂₀ to L₂₄ and L₂₀₁ are divalentlinking groups to be bonded to Az₂, L₂₀ to L₂₄ and L₂₀₁ are eachpreferably a substituted or unsubstituted divalent aromatic hydrocarbongroup. When g is 1 or more in the formula (2), not L₂₀ but L₂₀₁ is adivalent linking group to be bonded to Az₂.

Moreover, in the exemplary embodiment, when L₂₀ to L₂₄ and L₂₀₁ aredivalent linking groups to be bonded to Az₂, L₂₀ to L₂₄ and L₂₀₁ eachpreferably have a divalent six-membered ring structure, more preferablya divalent six-membered ring structure represented by a formula (2e),(2f) or (2g) below, further preferably a divalent six-membered ringstructure represented by the formula (2e) below.

In the formulae (2e) to (2g), X₄₁ to X₄₄ each independently representCR₅₂ or a nitrogen atom, in which R₅₂ each independently represents thesame as R₈ in the formula (1).

In the exemplary embodiment, X₄₁ to X₄₄ of the formulae (2e) to (2g) areeach independently preferably CR₅₂, in which R₅₂ is more preferably ahydrogen atom, alkyl group, alkoxy group, aryloxy group, cyano group,halogen atom and silyl group.

When g is 1 in the formula (2), L₂₀₁ preferably has a divalentsix-membered ring structure represented by the formula (2e) and L₂₀ ispreferably a heterocyclic group having 5 to 30 ring atoms. In thisarrangement, the heterocyclic group is preferably a carbazolyl group, inwhich a nitrogen atom at a position 9 of the carbazolyl group ispreferably bonded to L₂₀₁. Further preferably, at least one of thestructures represented by the formulae (2b) and (2bx) is bonded to thecarbazolyl group.

Moreover, L₂₁ of the formula (21), L₂₂ of the formula (22), L₂₃ and L₂₄of the formula (23) and L₂₀₁ of the formula (24) each preferably have adivalent six-membered ring structure represented by the formula (2e).

Specific examples of the compound represented by the formula (2) areshown below, but the invention is not limited thereto.

Also in the organic EL device of the third exemplary embodiment, thedrive voltage can be reduced and the emission lifetime can be prolongedin the same manner as in the above exemplary embodiments.

Modifications of Embodiment(s)

It should be noted that the invention is not limited to the aboveexemplary embodiments but may include any modification and improvementas long as such modification and improvement are compatible with theinvention.

The emitting layer is not limited to a single layer, but may be providedas laminate by a plurality of emitting layers. When the organic ELdevice includes the plurality of emitting layers, it is only requiredthat at least one of the emitting layers includes the compoundrepresented by the formula (1) and the compound represented by theformula (2). The rest of the emitting layers may be a fluorescentemitting layer or a phosphorescent emitting layer.

When the organic EL device includes the plurality of emitting layers,the plurality of emitting layers may be adjacent to each other, or maybe laminated on each other via an intermediate layer, a so-called tandemorganic EL device.

When the plurality of emitting layers are laminated, an organic ELdevice 1A is exemplarily shown in FIG. 4. The organic EL device 1Aincludes an organic layer 10A. The organic EL device 1A is differentfrom organic EL device 1 shown in FIG. 1 in that the organic layer 10Ahas a first emitting layer 51 and a second emitting layer 52 between thehole injecting/transporting layer 6 and the electroninjecting/transporting layer 7. At least one of the first emitting layer51 and the second emitting layer 52 contains the compound represented bythe formula (1) and the compound represented by the formula (2). As forother points, the organic EL device 1A is formed in the same manner asthe organic EL device 1.

The electron blocking layer may be provided to the emitting layeradjacent to the anode while the hole blocking layer may be providedadjacent to the emitting layer near the cathode. With this arrangement,the electrons and the holes can be trapped in the emitting layer,thereby enhancing probability of exciton generation in the emittinglayer.

The organic EL device of the invention is suitably applicable to anelectronic device such as: a display component of an organic EL panelmodule and the like, a display device of a television, a mobile phone, apersonal computer and the like; and an emitting unit of an illuminatoror a vehicle light.

Further, the specific arrangement and disposition for practicing theinvention may be altered to other arrangements and treatments as long assuch other arrangements and dispositions are compatible with theinvention.

EXAMPLES

Examples of the invention will be described below. However, theinvention is not limited by these Examples.

Compounds used in Examples for preparing the organic EL device will beshown as follows.

Evaluation of Compounds

Next, properties of the compounds used in Example were measured. Themeasurement target compounds are the compounds H1 to H6. A measurementmethod or a calculation method is described below. Measurement resultsor calculation results are shown in Table 1.

(Measurement 1) Singlet Energy EgS

Singlet Energy EgS was obtained by the following method.

A 100 nm thick film of each of the compounds was formed on a quartzsubstrate by vacuum deposition to provide a measurement sample. Emissionspectrum of each sample was measured at a room temperature (300K). Theemission spectrum was expressed in coordinates of which ordinate axisindicated the luminous intensity and of which abscissa axis indicatedthe wavelength. A tangent was drawn to the rise of the emission spectrumon the short-wavelength side, and a wavelength value λedge (nm) at anintersection of the tangent and the abscissa axis was obtained. Thewavelength value was converted to an energy value by the followingconversion equation. The energy value was defined as EgS.

EgS (eV)=1239.85/λedge  Conversion Equation:

For the emission spectrum measurement, a spectrophotofluorometer bodyF-7000 (manufactured by Hitachi High-Technologies Corporation) was used.

The tangent to the rise of the emission spectrum on the short-wavelengthside was drawn as follows. While moving on a curve of the emissionspectrum from the short-wavelength side to the maximum spectral valueclosest to the short-wavelength side among the maximum spectral values,a tangent is checked at each point on the curve toward thelong-wavelength of the emission spectrum. An inclination of the tangentis increased as the curve rises (i.e., a value of the ordinate axis isincreased). A tangent drawn at a point of the maximum inclination wasdefined as the tangent to the rise of the phosphorescence spectrum onthe short-wavelength side.

The maximum with peak intensity being 10% or less of the maximum peakintensity of the spectrum is not included in the above-mentioned maximumclosest to the short-wavelength side of the spectrum. The tangent drawnat a point of the maximum spectral value being closest to theshort-wavelength side and having the maximum inclination is defined as atangent to the rise of the emission spectrum on the short-wavelengthside.

(Measurement 2) Energy Gap Eg_(77K)

Eg_(77K) was obtained by the following method.

Energy gap Eg_(77K) of each of the compounds H1 to H5 is measured asfollows.

Each of the measurement target compounds and a compound TH-2 below wereco-deposited on a quartz substrate by vacuum deposition to prepare asample encapsulated in an NMR tube. The samples were prepared under thefollowing conditions.

quartz substrate/TH-2: measurement target compound (100 nm of thickness,12 mass % of concentration of the measurement target compound)

The compound H6 was deposited on a quartz substrate by vacuum depositionto prepare a sample encapsulated in an NMR tube.

A phosphorescent spectrum (ordinate axis: phosphorescent luminousintensity, abscissa axis: wavelength) of each of the samples wasmeasured at a low temperature (77K). A tangent was drawn to the rise ofthe phosphorescent spectrum on the short-wavelength side. An energyamount was calculated as the energy gap Eg_(77K) at 77K according to aconversion equation 2 below based on a wavelength value λ_(edge) (nm) atan intersection of the tangent and the abscissa axis.

Eg _(77K) (eV)=1239.85/λ_(edge)  Conversion Equation 2:

For phosphorescence measurement, a spectrophotofluorometer body F-4500(manufactured by Hitachi High-Technologies Corporation) was used.

The tangent to the rise of the phosphorescence spectrum on theshort-wavelength side is drawn as follows. While moving on a curve ofthe phosphorescence spectrum from the short-wavelength side to themaximum spectral value closest to the short-wavelength side among themaximum spectral values, a tangent is checked at each point on the curvetoward the long-wavelength of the phosphorescence spectrum. Aninclination of the tangent is increased as the curve rises (i.e., avalue of the ordinate axis is increased). A tangent drawn at a point ofthe maximum inclination (i.e., a tangent at an inflection point) isdefined as the tangent to the rise of the phosphorescence spectrum onthe short-wavelength side.

The maximum with peak intensity being 15% or less of the maximum peakintensity of the spectrum is not included in the above-mentioned maximumclosest to the short-wavelength side of the spectrum. The tangent drawnat a point of the maximum spectral value being closest to theshort-wavelength side and having the maximum inclination is defined as atangent to the rise of the phosphorescence spectrum on theshort-wavelength side.

The material used in the exemplary embodiment is preferably a compoundhaving a small ΔST. When ΔST is small, intersystem crossing and inverseintersystem crossing are likely to occur even at a low temperature(77K), so that the singlet state and the triplet state coexist. As aresult, the spectrum to be measured in the same manner as the aboveincludes emission from both the singlet state and the triplet state.Although it is difficult to distinguish the emission from the singletstate from the emission from the triplet state, the value of the tripletenergy is basically considered dominant.

Accordingly, in the exemplary embodiment, the spectrum is measured bythe same method as a typical triplet energy is measured, but an energyvalue of the spectrum measured in the aforementioned manner is referredto as an energy gap Eg_(77K) in order to differentiate the measuredenergy from a typical triplet energy in a strict meaning.

(Measurement 3) ΔST

ΔST was obtained as a difference between EgS and Eg_(77K) respectivelymeasured in the above (Measurement 1) and (Measurement 2) (see the abovenumerical formula (2)).

The results are shown in Table 1.

(Measurement 4) Delayed Fluorescence

Delayed fluorescence was checked by measuring transitional PL using thedevice shown in FIG. 2. A measurement target compound and the compoundTH-2 were co-deposited on a quartz substrate so that a ratio of themeasurement target compound was 12 mass % to prepare a 100 nm thin-filmsample. The measurement target compounds were the compounds H1 to H5.

Delayed fluorescence can be obtained using the device of FIG. 2. Afterthe measurement target compounds are excited with pulse light (lightirradiated from the pulse laser) having a wavelength to be absorbed inthe measurement target compounds, Prompt Emission that is immediatelyobserved in the excited state and Delay Emission that is not observedimmediately after the excitation and is later observed are present. Inthe exemplary embodiments, delayed fluorescence means that an amount ofDelay Emission is 5% or more based on an amount of Prompt Emission. Ithas been confirmed that the amount of Delay Emission is 5% or more basedon the amount of Prompt Emission in the compounds H1 to H5 of themeasurement target compounds.

The amount of Prompt Emission and the amount of Delay Emission can beobtained according to the method as a method described in “Nature 492,234-238, 2012.”

A device used for calculating the amounts of Prompt Emission and DelayEmission is not limited to the device of FIG. 2 and a device describedin the above document.

TABLE 1 Compounds EgS (eV) Eg_(77K) (eV) ΔST (eV) H1 2.85 2.72 0.13 H22.67 2.46 0.21 H3 2.95 2.70 0.25 H4 3.00 2.75 0.25 H5 3.00 2.86 0.14 H64.36 3.50 0.86

Preparation and Evaluation 1 of Organic EL Device

The organic EL device was prepared and evaluated as follows.

Example 1

A glass substrate (size: 25 mm×75 mm×0.1 mm thick, manufactured byGeomatec Co., Ltd.) having an ITO transparent electrode (anode) wasultrasonic-cleaned in isopropyl alcohol for five minutes, and thenUV/ozone-cleaned for 30 minutes. A film of ITO was 130 nm thick.

After the glass substrate having the transparent electrode line wascleaned, the glass substrate was mounted on a substrate holder of avacuum evaporation apparatus. Initially, a compound H1 was evaporated ona surface of the glass substrate where the transparent electrode linewas provided in a manner to cover the transparent electrode, therebyforming a 5 nm thick film of the compound H1. The H1 film serves as ahole injecting layer.

After the film formation of the H1 film, the compound HT-1 was depositedon the H1 film to form a 160 nm thick HT-1 film. The HT-1 film serves asa first hole transporting layer.

The compound HT-2 was further deposited on the HT-1 film to form a 10 nmthick HT-2 film. The HT-2 film serves as a second hole transportinglayer.

The compound H1 and the compound H2 were co-deposited on the HT-2 filmto form a 35 nm thick emitting layer. The concentration of the compoundH1 in the emitting layer was set at 94 mass % and the concentration ofthe compound H2 in the emitting layer was set at 6 mass %.

The compound ET-1 was deposited on the emitting layer to form a 5 nmthick ET-1 film. The ET-1 film serves as a first electron transportinglayer.

The compound ET-2 was deposited on the ET-1 film to form a 25 nm thickET-2 film. The ET-2 film serves as a second electron transporting layer.

LiF was deposited on the ET-2 film to form a 1 nm thick LiF film.

A metal Al was deposited on the LiF film to form an 80 nm thick metalcathode.

A device arrangement of the organic EL device in Example 1 is shown insymbols as follows.

ITO(130)/H1(5)/HT-1(160)/HT-2(10)/H1:H2(35,94%:6%)/ET-1(5)/ET-2(25)/LiF(1)/Al(80)

Numerals in parentheses represent a film thickness (unit: nm). Thenumerals represented by percentage in parentheses indicate a ratio (masspercentage) of the compounds in the emitting layer. The same applies toExamples and Comparatives below.

Example 2

An organic EL device in Example 2 was manufactured in the same manner asin Example 1 except that the concentration of the compound H1 waschanged to 88 mass % and the concentration of the compound H2 waschanged to 12 mass % in the emitting layer of the organic EL device inExample 1.

A device arrangement of the organic EL device in Example 2 is shown insymbols as follows.

ITO(130)/H1(S)/HT-1(160)/HT-2(10)/H1:H2(35,88%:12%)/ET-1(5)/ET-2(25)/LiF(1)/Al(80)

(

)

An organic EL device in Example 3 was manufactured in the same manner asin Example 1 except that the compound H1 was replaced by a compound H3in the emitting layer of the organic EL device in Example 1.

A device arrangement of the organic EL device in Example 3 is shown insymbols as follows.

ITO(130)/H1(5)/HT-1(160)/HT-2(10)/H3:H2(35,94%:6%)/ET-1(5)/ET-2(25)/LiF(1)/Al(80)

Numerals in parentheses represent a film thickness (unit: nm). Numeralsrepresented by percentage in the same parentheses represent a ratio(mass %) of an added component such as the dopant material in theemitting layer.

Example 4

An organic EL device in Example 4 was manufactured in the same manner asin Example 1 except that the compound H1 was replaced by the compound H3and the concentration of the compound H2 was changed to 12 mass % in theemitting layer of the organic EL device in Example 1.

A device arrangement of the organic EL device in Example 6 is shown insymbols as follows.

ITO(130)/H1(5)/HT-1(160)/HT-2(10)/H3:H2(35,88%:12%)/ET-1(5)/ET-2(25)/LiF(1)/Al(80)

Numerals in parentheses represent a film thickness (unit: nm). Numeralsrepresented by percentage in the same parentheses represent a ratio(mass %) of an added component such as the dopant material in theemitting layer.

Comparative 1

An organic EL device in Comparative 1 was manufactured in the samemanner as in Example 1 except that a compound 1 was replaced by CBP inthe emitting layer of the organic EL device in Example 1.

A device arrangement of the organic EL device in Comparative 1 is shownin symbols as follows.

ITO(130)/H1(5)/HT-1(160)/HT-2(10)/CBP:H2(35,94%:6%)/ET-1(5)/ET-2(25)/LiF(1)/Al(80)

Comparative 2

An organic EL device in Comparative 2 was manufactured in the samemanner as in Example 1 except that the compound 1 was replaced by CBPand the concentration of the compound H2 was changed to 12 mass % in theemitting layer of the organic EL device in Example 1.

A device arrangement of the organic EL device in Comparative 2 is shownin symbols as follows.

ITO(130)/H1(5)/HT-1(160)/HT-2(10)/CBP:H2(35,88%:12%)/ET-1(5)/ET-2(25)/LiF(1)/Al(80)

Evaluation of Organic EL Devices

The prepared organic EL devices of Examples 1 to 4 and Comparatives 1 to2 were evaluated as follows. The evaluation results are shown in Table2.

Drive Voltage

Voltage was applied between ITO transparent electrode and Al metalcathode such that a current density was 10 mA/cm², where the voltage(unit: V) was measured.

Luminance and CIE1931 Chromaticity

Voltage was applied on each of the organic EL devices such that thecurrent density was 10 mA/cm², where luminance and coordinates ofCIE1931 chromaticity were measured by a spectroradiometer (CS-1000manufactured by Konica Minolta, Inc.).

Current Efficiency L/J and Power Efficiency η

Voltage was applied on each of the organic EL devices such that thecurrent density was 10.00 mA/cm², where spectral radiance spectra weremeasured by the aforementioned spectroradiometer. Based on the obtainedspectral radiance spectra, the current efficiency (unit: cd/A) and thepower efficiency η (unit: lm/W) were calculated.

Main Peak Wavelength λ_(p)

A main peak wavelength λ_(p) was calculated based on the obtainedspectral-radiance spectra.

External Quantum Efficiency EQE

Voltage was applied on each of the organic EL devices such that thecurrent density was 10 mA/cm², where spectral radiance spectrum wasmeasured by a spectroradiometer (CS-1000 manufactured by Konica Minolta,Inc.). The external quantum efficiency EQE (unit: %) was calculatedbased on the obtained spectral-radiance spectra, assuming that thespectra were provided under a Lambertian radiation.

TABLE 2 Current Density Voltage Luminance L/J η λ_(p) EQE [mA/cm²] [V][cd/m²] [cd/A] [I/W] Chromaticity x Chromaticity y [nm] [%] Example 1 103.73 5883.2 58.83 49.58 0.373 0.579 541 17.41 Example 2 10 3.74 5981.759.82 50.21 0.384 0.579 545 17.59 Example 3 10 3.93 4917.7 49.18 39.340.372 0.574 544 14.64 Example 4 10 3.89 5163.1 51.63 41.68 0.384 0.575545 15.36 Comparative 1 10 6.70 4452.6 44.52 20.87 0.363 0.578 543 13.22Comparative 2 10 5.77 5067.6 50.68 27.61 0.381 0.577 544 15.07

As shown in Table 2, it was found that the organic EL devices ofExamples 1 to 4 including the emitting layer containing the compounds H1and H2 emitting thermally activated delayed fluorescence emitted lightat a lower drive voltage with a higher efficiency than the drive voltageand the efficiency of the organic EL devices of Comparatives 1 to 2containing CBP.

Preparation and Evaluation 2 of Organic EL Device Example 5

An organic EL device in Example 5 was manufactured in the same manner asin Example 2 except that the compound H2 was replaced by the compound H4and the thickness of the emitting layer was changed to 30 nm in theemitting layer of the organic EL device in Example 2.

A device arrangement of the organic EL device in Example 5 is shown insymbols as follows.

ITO(130)/H1(5)/HT-1(160)/HT-2(10)/H1:H4(30,88%:12%)/ET-1(5)/ET-2(25)/LiF(1)/Al(80)

Example 6

An organic EL device in Example 6 was manufactured in the same manner asin Example 5 except that the concentration of the compound H1 waschanged to 76 mass % and the concentration of the compound H4 waschanged to 24 mass % in the emitting layer of the organic EL device inExample 5.

A device arrangement of the organic EL device in Example 6 is shown insymbols as follows.

ITO(130)/H1(5)/HT-1(160)/HT-2(10)/H1:H4(30,76%:24%)/ET-1(5)/ET-2(25)/LiF(1)/Al(80)

Example 7

An organic EL device in Example 7 was manufactured in the same manner asin Example 1 except that the emitting layer of the organic EL device inExample 1 was formed as follows.

The compounds H1, H4 and H5 were co-deposited on the HT-2 film to form a30 nm thick emitting layer. The concentration of the compound H1 was setat 33 mass %, the concentration of the compound H4 was set at 33 mass %,and the concentration of the compound H5 was set at 34 mass % in theemitting layer.

A device arrangement of the organic EL device in Example 7 is shown insymbols as follows.

ITO(130)/H1(5)/HT-1(160)/HT-2(10)/H1:H4:H5 (30,33%:33%:34%)/ET-1(5)/ET-2(25)/LiF(1)/Al(80)

Comparative 3

An organic EL device in Comparative 3 was manufactured in the samemanner as in Example 1 except that the thickness of the emitting layerwas changed to 30 nm, the concentration of the compound H1 was changedto 88 mass %, and the concentration of the compound H4 was changed to 12mass % in the emitting layer of the organic EL device in Example 1.

A device arrangement of the organic EL device in Comparative 3 is shownin symbols as follows.

ITO(130)/H1(5)/HT-1(160)/HT-2(10)/H1:H6(30,12%:88%)/ET-1(5)/ET-2(25)/LiF(I)/Al(80)

Evaluation of Organic EL Devices

The prepared organic EL devices in Examples 5 to 7 and Comparative 3were measured in terms of drive voltage, luminance, CIE1931chromaticity, and main peak wavelength λ_(p) according to the samemethod as the above, and further in terms of lifetime according to thefollowing method.

Lifetime LT50 (Examples 5, 6 and Comparative 3)

Voltage was applied to the devices and a time until an initial luminance(1000 cd/m²) was decreased in half was defined as the lifetime (unit:h).

Lifetime LT50 (Example 7)

Constant current of 50 mA/cm² was applied to the devices and a timeuntil an initial luminance was decreased in half was defined as thelifetime (unit: h). Note that a time until an initial luminance (1000cd/m²) was decreased in half assuming that an acceleration factor is 1.8was described in LT50 of Table 3.

TABLE 3 Current Density Voltage Luminance λ_(p) LT50 [mA/cm²] [V][cd/m²] Chromaticity x Chromaticity y [nm] ┌h┘ Example 5 10 3.85 1981.70.199 0.429 497 186 Example 6 10 3.87 1834.4 0.194 0.414 495 176 Example7 10 3.60 1363.5 0.191 0.359 484 50 Comparative 3 10 6.24 1761.4 0.1960.411 494 <1

As shown in Table 3, it was found that the organic EL devices ofExamples 5 to 7 including the emitting layer containing the compounds H1and H2 emitting thermally activated delayed fluorescence emitted lightat a lower drive voltage with a longer lifetime than the drive voltageand the lifetime of the organic EL device of Comparative 3. It was foundthat, when the compound H6 was contained as a main component in theemitting layer instead of the compound H2 emitting thermally activateddelayed fluorescence as in the organic EL device of Comparative 3, thedrive voltage was high and the lifetime was short.

EXPLANATION OF CODES

-   1 . . . organic EL device-   2 . . . substrate-   3 . . . anode-   4 . . . cathode-   5 . . . emitting layer-   6 . . . hole injecting/transporting layer-   7 . . . electron injecting/transporting layer-   10 . . . organic layer

1. An organic electroluminescence device, comprising: an anode; acathode; and an emitting layer, wherein the emitting layer comprises afirst compound and a second compound, and each of the first compound andthe second compound is a compound emitting thermally activated delayedfluorescence.